CN112300042B - 4-苯并五元环-苯基硫鎓盐类化合物及其制备方法和应用 - Google Patents
4-苯并五元环-苯基硫鎓盐类化合物及其制备方法和应用 Download PDFInfo
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- CN112300042B CN112300042B CN202011035167.3A CN202011035167A CN112300042B CN 112300042 B CN112300042 B CN 112300042B CN 202011035167 A CN202011035167 A CN 202011035167A CN 112300042 B CN112300042 B CN 112300042B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 17
- -1 (4-(benzo [d] thiophen-2-yl) phenyl) dimethyl sulfonium salt-hexafluorophosphate Chemical compound 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000002244 precipitate Substances 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 238000004809 thin layer chromatography Methods 0.000 claims description 4
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 3
- QRVYABWJVXXOTN-UHFFFAOYSA-N 4-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(C=O)C=C1 QRVYABWJVXXOTN-UHFFFAOYSA-N 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 2
- UGPIYNNXFIUSQU-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)-1,3-benzothiazole Chemical compound C1=CC(SC)=CC=C1C1=NC2=CC=CC=C2S1 UGPIYNNXFIUSQU-UHFFFAOYSA-N 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 9
- 238000000016 photochemical curing Methods 0.000 abstract description 8
- 239000011248 coating agent Substances 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910018286 SbF 6 Inorganic materials 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
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- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 238000009396 hybridization Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 229960004756 ethanol Drugs 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 235000021286 stilbenes Nutrition 0.000 description 5
- IVUHTLFKBDDICS-UHFFFAOYSA-N (4-methylsulfanylphenyl)boronic acid Chemical compound CSC1=CC=C(B(O)O)C=C1 IVUHTLFKBDDICS-UHFFFAOYSA-N 0.000 description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- OGMMQOPUZNLKGU-UHFFFAOYSA-N 2-bromo-6-methoxy-1-benzofuran Chemical compound COc1ccc2cc(Br)oc2c1 OGMMQOPUZNLKGU-UHFFFAOYSA-N 0.000 description 3
- YFWQUMZOIMJBJN-UHFFFAOYSA-N 2-bromobenzo[e][1]benzofuran Chemical compound Brc1cc2c(ccc3ccccc23)o1 YFWQUMZOIMJBJN-UHFFFAOYSA-N 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000007699 photoisomerization reaction Methods 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- KQADGUUEZYYSLG-UHFFFAOYSA-N 2-(2,2-dibromoethenyl)-5-methoxyphenol Chemical compound COc1ccc(C=C(Br)Br)c(O)c1 KQADGUUEZYYSLG-UHFFFAOYSA-N 0.000 description 2
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 description 2
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N Benzylformate Chemical compound O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
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- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000003935 benzaldehydes Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical class Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
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- MEXOXAPBPRXNFI-UHFFFAOYSA-N 1-(2,2-dibromoethenyl)naphthalen-2-ol Chemical compound C1=CC=CC2=C(C=C(Br)Br)C(O)=CC=C21 MEXOXAPBPRXNFI-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- PKRRNTJIHGOMRC-UHFFFAOYSA-N 1-benzofuran-2-ylboronic acid Chemical compound C1=CC=C2OC(B(O)O)=CC2=C1 PKRRNTJIHGOMRC-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- XKQQFGSSJLXNRD-UHFFFAOYSA-N 1-methyl-4-[3-[3-(6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)prop-2-enoxy]prop-1-enyl]-7-oxabicyclo[4.1.0]heptane Chemical compound CC12C(CC(CC1)C=CCOCC=CC1CC3C(CC1)(O3)C)O2 XKQQFGSSJLXNRD-UHFFFAOYSA-N 0.000 description 1
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- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
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- XKOWGGVJZHBDJA-UHFFFAOYSA-N 2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCCC1CC2OC2CC1 XKOWGGVJZHBDJA-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
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- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D333/74—Naphthothiophenes
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- C07D495/04—Ortho-condensed systems
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
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Abstract
本申请4‑苯并五元环‑苯基硫鎓盐类化合物及其制备方法和应用，涉及下述式(I)所示的4‑苯并五元环‑苯基硫鎓盐衍生物、光固化组合物以及式(I)所示的4‑苯并五元环‑苯基硫鎓盐衍生物的制备方法。本发明的式(I)所示的4‑苯并五元环‑苯基硫鎓盐衍生物在与4‑苯乙烯‑苯基硫鎓盐相比，分子的光引发效率更好，而且合成步骤比较简单，有望成为UV‑Vis‑LED可激发的光固化涂料或油墨工业化的生产和应用的光引发剂。
Description
技术领域
本发明属于新材料有机化学品技术领域，具体涉及一种4-苯并五元环-苯基硫鎓盐类化合物及其制备方法和应用。
背景技术
光固化反应是指在光照(紫外或可见光)下，引发剂产生活性种(自由基或者阳离子等)引发多官能度的低聚物和/或活性稀释剂进行链式聚合反应，快速形成高度交联的聚合物网络，因此其具有快速高效、操作简便、可以实现时间-空间可控等优点，在被广泛应用于涂料、胶黏剂以及生物医药、3D打印等领域中，具有极高的商业价值。实现光固化的配方中通常含有光引发剂、活性稀释剂、低聚物和各种助剂，而配方体系中大多数单体都不能在光照作用下产生有效的引发活性种，因此，光引发剂成为光固化配方中至关重要的组分，其活性直接影响光固化速率、固化程度以及终端产品性能。
但是传统的光固化采用汞灯作为光源，能耗较高，而且会产生臭氧，破坏环境，不利于实现可持续发展，但是新兴的LED光源较汞灯波长较长，与传统的光引发剂吸收波长并不匹配，难以实现高效的光引发效率，为此开发一系列高效的LED光引发剂成为了新的研究热点。二苯乙烯及其衍生物由于具有良好的平面共轭结构，可以实现波长的红移，有望成为高感光性、高稳定性、且易于制备的LED光引发剂，如下结构所示。
这些分子结构的吸光基团由共轭的二苯乙烯结构组成，在LED发射光谱波段有很高的摩尔消光系数。但是，也不是没有缺点，二苯乙烯类结构中存在的双键在被光辐照时会发生光致异构化，与鎓盐的S-C键光解竞争，导致其吸收的能量有一部分无法用于分子激发断键，极大地影响了其光引发的效率。
因此，解决二苯乙烯类光引发剂双键光致异构化化导致引发效率受影响的问题，合成无光致异构化二苯乙烯类结构的对LED光源敏感的、在光固化领域中具有高感光性、稳定性高、且易于制备的光引发剂是我们要做的技术挑战。
发明内容
本发明人等针对现有分子结构中的不足进行了深入研究后发现，通过将五元环引入到硫鎓盐中获得的本发明的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物，可以保持双键的同时，其中五元环可以扼制双键的异构，从而解决二苯乙烯类光引发剂引发效率受影响的问题。又从C＝C双键出发，引入了C＝N双键等结构，进一步拓展了类似二苯乙烯类的分子结构。由此，本发明的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物有望成为新的高效率商品化的LED光源的光引发剂。
进一步，本发明的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物的制备方法不仅方法简便，并且产率高、原料易于获得，适合工业化的生产和应用。本发明的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物作为光生酸剂具有良好应用前景。
具体地，本发明提供下述方案：
第一方面，本发明提供下述的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物，其通式如下：
其中：
R1，R2，R3，R4分别独立地选自未取代或者被1-4个Ra取代的C1-6的烷基、-F、-Cl、-Br、-I、-CN、-CF2CF3、-CF3、-NO2、-NRbRb、-ORb、-SRb、-C(＝O)Rb、-CO2Rb、-OC(＝O)Rb、-NRbC(＝O)Rb、-S(＝O)Rb、-S(＝O)2Rb；两者同时存在时也可以组成环状结构的苯并芳环、苯并芳杂环、苯并二氧五环；
R5、R6各自独立地选自C1-12的烷基或者被1-5个R7取代的苄基或者被1-5个R7取代的苯基；
R7选自被1-5个Ra取代的C1-6的烷基、-F、-Cl、-Br、-I、-CN、-CF2CF3、-CF3、-NO2、-NRbRb、-ORb、-SRb、-C(＝O)Rb、-CO2Rb、-OC(＝O)Rb、-NRbC(＝O)Rb、-S(＝O)Rb、-S(＝O)2Rb或者被1-5个Rc取代的碳环，被1-5个Rd取代的杂环、或者、P(＝O)(ORb)2；
Ra选自C1-6烷基、(CH2)rC3-6环烷基或者-(CH2)r苯基；
Rb选自H或者被1-5个Re取代的C1-6烷基，或者被1-5个Re取代的-(CH2)rPh；
Rc选自被1-5个Re取代的C1-6烷基或者被1-5个Re取代的(CH2)rPh；
Rd选自被1-5个Re取代的C1-6烷基，或者被1-5个Re取代的(CH2)rPh；
Re选自-F、-Cl、-Br、-I、-OH、-NO2、-CN，-CF3、-CF2CF3、C1-4烷基、C1-4烷氧基、C3-7环烷基、苯基、苄基、苯乙基、萘基、杂环芳基、或者、酮基；
r为0、1、2、3或者4；
X、Y各自独立地选自CH、CH2、O、N、NH、NRf、S、SO、SO2、Se和SeO2；
Rf选自C1-12烷基、C3-7环烷基、苯基、苄基、苯乙基、萘基、杂环芳基；
Z-为阴离子，选自Cl-、CF3SO3 -、CH3SO3 -、p-MePhSO3 -、BF4 -、B(Ph)4 -、B(PhF5)4 -、PF6 -、SbF6 -、或者Al(Perfluoro-t-BuO)4 -；
硫鎓盐在苯环上的取代位置可以是对位也可以是间位。
第二方面，本发明提供一种光固化组合物，其含有本发明的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物和可聚合成分，所述可聚合成分包含具有烯键或者环氧基的单体或聚合物。
第三方面，本发明提供式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物的制备方法。
方法一
一种4-苯并五元环-苯基硫鎓盐衍生物的五元杂化中X或者Y包括CH或CH2时，所述式(I)-a所示的化合物的制备方法，特征是，包括步骤步骤(a)、步骤(b)、步骤(c)合：
所述步骤(a)：
所述步骤(a)中硼酸衍生物和溴代芳基衍生物在钯催化剂和碱性条件下反应，得到中间体(I)-a，反应温度为室温20℃～150℃；
所述步骤(b)中的4-苯并五元环-苯基硫醚和含有R6取代基的三氟甲磺酸酯在无水无氧的条件下反应，得到中间体(I)-b，反应温度为0℃～室温20℃；
所述步骤(c)中，将前述反应体系——式(I)-b所示的化合物与R5、R6取代硫鎓盐加入到含有以Metal+Z-表示的含金属元素化合物的水溶液中经盐交换反应，分离析出的沉淀，将所述沉淀重结晶得到所述式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物；
所述R1、R2、R3、R4、R5、R6、X、Y、Z的定义与权利要求1和2中相同。
方法二
一种所述的4-苯并五元环-苯基硫鎓盐衍生物的五元杂化中X和Y为CH和CH2时，所述式(I)-a所示的化合物的制备方法，特征是，包括步骤步骤(a’)、步骤(b)、步骤(c)合：
所述步骤(a’)获得：
所述步骤(a’)中，取代茚酮溶解在乙醚中与取代苯溴化镁反应得到(I)-a所示化合物，反应温度为室温20℃～65℃；
所述步骤(b)中的4-苯并五元环-苯基硫醚和含有R6取代基的三氟甲磺酸酯在无水无氧的条件下反应，得到中间体(I)-b，反应温度为0℃～室温20℃；
所述步骤(c)中，将前述反应体系——式(I)-b所示的化合物与R5、R6取代硫鎓盐加入到含有以Metal+Z-表示的含金属元素化合物的水溶液中经盐交换反应，分离析出的沉淀，将所述沉淀重结晶得到所述式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物；
所述R1、R2、R3、R4、R5、R6、X、Y、Z的定义与权利要求1和2中相同。
方法三
一种所述的4-苯并五元环-苯基硫鎓盐衍生物的五元杂化中Y是N时，所述式(I)-a所示的化合物的制备方法，特征是，包括步骤步骤(a”)、步骤(b)、步骤(c)合：
所述步骤(a”)获得：
所述步骤(a”)中，邻酚取代苯胺在无水乙醇中以含锌的盐或者氧化物为催化剂与取代苯甲醛反应得到(I)-a所示化合物，反应温度为室温20℃～60℃；
步骤(b)中的4-苯并五元环-苯基硫醚和含有R6取代基的三氟甲磺酸酯在无水无氧的条件下反应，得到中间体(I)-b，反应温度为0℃～室温20℃；
步骤(c)中，将前述反应体系——式(I)-b所示的化合物与R5、R6取代硫鎓盐加入到含有以Metal+Z-表示的含金属元素化合物的水溶液中经盐交换反应，分离析出的沉淀，将所述沉淀重结晶得到所述式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物；
所述R1、R2、R3、R4、R5、R6、X、Y、Z的定义与权利要求1和2中相同。
本发明的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物作为光生酸剂具有良好应用前景，其能够用作光引发剂应用于光固化组合物中，也可以作为合成其他化合物的中间体。另外，本发明的4-苯并五元环-苯基硫鎓盐及其衍生物还作为辐射固化光敏引发剂能够在辐射固化配方产品中应用，特别是在UV-Vis-LED可激发的光固化涂料或油墨等场合应用。
本发明的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物的制造方法，分子的合成步骤简便，原材料容易获得，适合工业化的生产和应用。
前述术语“C1-12的烷基”是指碳原子数为1～12个的烷基，其可以为直链或支链的烷基，没有特别的限定。作为“C1-12的烷基”的实例，可以列举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基等。
前述术语“C1-6的烷基”是指碳原子数为1～6个的烷基，其可以为直链或支链的烷基，没有特别的限定。作为“C1-6的烷基”的实例，可以列举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基、己基等。
前述术语“杂环芳基”是指具有芳香特性的杂环基，作为芳香杂环基的实例，可以列举出呋喃基、咪唑基、吡啶基等。
前述术语“苯并芳香杂环基”是指苯环与杂环稠合而成的芳香杂环基，作为“苯并芳香杂环基”的实例，例如有喹啉基、吲哚基、嘌呤基等。
前述术语“C3-7环烷基”是指碳原子数为3～7个的环烷基，作为“C3-7环烷基”的实例，例如有环丙基、甲基环丙基、环丁基、环戊基、甲基环丁基、二甲基环丁基、环己基等。
前述术语“C1-4烷基”是指碳原子数为1～4个的烷基，作为“C1-4的烷基”的实例，可以列举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基。
前述术语“C1-4烷氧基”是指碳原子数为1～4个的含氧原子的烷基，作为“C1-4的烷基”的实例，可以列举出例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基。
前述的“Ph”表示苯基。
本发明的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物中，优选地，R5、R6各自独立地选自甲基、环丙基、苯基、苄基、4-氰基苄基、或者、4-三氟甲基苄基。由此，所获得的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物不仅制造成本低，进一步，这样的硫鎓盐在光解后产生自由基、阳离子，可以引发自由基聚合、阳离子聚合。
本发明的式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物中，含X、Y的五元环选自下述的结构式之一：
本发明式(I)所述的4-苯并五元环-苯基硫鎓盐衍生物，其选自下述的结构式所示的化合物组成的组:
其中，Z-为阴离子。
本发明的式(I)所示4-苯并五元环-苯基硫鎓盐中，优选地，Z-选自卤素、含氧酸根、硼酸根、磷酸根、锑酸根、或者、铝酸根。进一步优选地，Z-选自Cl-、CF3SO3 -、p-MePhSO3 -、BF4 -、B(Ph)4 -、B(PhF5)4 -、PF6 -、SbF6 -、AsF6 -、或者、Al(Perfluoro-t-Bu)4 -。
[光固化组合物]
本发明的光固化组合物含有前述的本发明的4-苯并五元环-苯基硫鎓盐及其衍生物和可聚合成分，前述可聚合成分包含具有烯键或者环氧基的单体或聚合物。
本发明的光固化组合物中，优选地，相对于所述可聚合成分的总量100重量份，前述式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物的含量为0.1～15重量份。更优选地，前述式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物的含量为0.5～10重量％。
作为前述的具有烯键的单体，例如可以列举出例如，(甲基)丙烯酸酯，丙烯醛，烯烃，共轭双烯烃，苯乙烯，马来酸酐，富马酸酐，乙酸乙烯酯，乙烯基吡咯烷酮，乙烯基咪唑，(甲基)丙烯酸，(甲基)丙烯酸衍生物例如(甲基)丙烯酰胺，乙烯基卤化物，亚乙烯基卤化物等。
作为前述的具有环氧基的单体，例如可以列举出例如单官能缩水甘油醚类、多官能脂肪族缩水甘油醚类、多官能芳香族缩水甘油醚类、缩水甘油酯类、脂肪族环氧化合物等。
作为单官能缩水甘油醚类，例如可以列举出，烯丙基缩水甘油醚、丁基缩水甘油醚、苯基缩水甘油醚、2-乙基己基缩水甘油醚、仲丁基苯基缩水甘油醚、叔丁基苯基缩水甘油醚、2-甲基辛基缩水甘油醚等。
作为多官能脂肪族缩水甘油醚类，可以列举出例如，1,6-己二醇缩水甘油醚、三羟甲基丙烷三缩水甘油醚、新戊二醇二缩水甘油醚、甘油二缩水甘油醚、甘油三缩水甘油醚、乙二醇二缩水甘油醚、聚乙二醇二缩水甘油醚、聚丙二醇二缩水甘油醚等。
作为多官芳香族缩水甘油醚类，可以列举出例如，双酚A缩水甘油醚、双酚F缩水甘油醚、溴化双酚A缩水甘油醚、联苯酚缩水甘油醚、四甲基联苯酚缩水甘油醚、间苯二酚缩水甘油醚等。
作为缩水甘油酯类，可以列举出例如，丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯、邻苯二甲酸二缩水甘油酯、六氢邻苯二甲酸二缩水甘油酯等。
作为脂肪族环氧化合物，可以列举出例如，3,4-环氧环己基甲基-3,4-环氧环己基甲酸酯、3,4-环氧环己基乙基-3,4-环氧环己基甲酸酯、乙烯环己烯基二氧化物、丙烯基环己烯基二氧化物、3,4-环氧-4-甲基环己基-2-丙烯基氧化物等。
本发明的光固化组合物中，前述的可聚合成分也可以为低聚物或预聚物等聚合物的形式，或者是由单体、低聚物、预聚物中的至少一种形成的共聚物。另外，也可以是水性分散体的形式。
作为这样的含烯键的聚合物，可以列举出例如(甲基)丙烯酰官能基的(甲基)丙烯酸共聚物，聚氨酯甲酸酯(甲基)丙烯酸酯，聚酯(甲基)丙烯酸酯，不饱和聚酯，聚醚(甲基)丙烯酸酯，硅氧烷(甲基)丙烯酸酯，环氧树脂(甲基)丙烯酸酯等，以及上述物质的水溶性或水分散性的类似物。
作为前述的含环氧基的聚合物，例如可以是含有环氧基的聚合物或者树脂，如双酚A环氧树脂、二环戊二烯型环氧树脂、二氨基二苯基甲烷型环氧树脂、氨基苯酚型环氧树脂、萘型环氧树脂、酚醛清漆型环氧树脂、联苯型环氧树脂、氢化联苯型环氧树脂、脂肪式环氧树脂等。
[4-苯并五元环-苯基硫鎓盐及其衍生物的制备方法]
本发明提供式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物的制备方法，其包括如下的步骤：
当所述的4-苯并五元环-苯基硫鎓盐衍生物的五元杂化中X或者Y包括CH或CH2时，所述式(I)-a所示的化合物的制备方法包括下述步骤(a)：
所述步骤(a)中硼酸衍生物和溴代芳基衍生物在钯催化剂和碱性条件下反应，得到中间体(I)-a，反应温度为室温20℃～150℃；
当所述的4-苯并五元环-苯基硫鎓盐衍生物的五元杂化中X和Y为CH和CH2时，所述式(I)-a所示的化合物的制备方法是由下述步骤(a’)获得：
所述步骤(a’)中，取代茚酮溶解在乙醚中与取代苯溴化镁反应得到(I)-a所示化合物，反应温度为室温20℃～65℃
当所述的4-苯并五元环-苯基硫鎓盐衍生物的五元杂化中Y是N时，所述式(I)-a所示的化合物的制备方法通过下述步骤(a”)获得：
所述步骤(a”)中，邻酚取代苯胺在无水乙醇中以含锌的盐或者氧化物为催化剂与取代苯甲醛反应得到(I)-a所示化合物，反应温度为室温20℃～60℃；
所述的4-苯并五元环-苯基硫鎓盐衍生物的由式(I)-a所示化合物经步骤(b)、步骤(c)合成：
所述步骤(b)中的4-苯并五元环-苯基硫醚和含有R6取代基的三氟甲磺酸酯在无水无氧的条件下反应，得到中间体(I)-b，反应温度为0℃～室温20℃。
所述步骤(c)中，将前述反应体系——式(I)-b所示的化合物与R5、R6取代硫鎓盐加入到含有以Metal+Z-表示的含金属元素化合物的水溶液中经盐交换反应，分离析出的沉淀，将所述沉淀重结晶得到所述式(I)所示的4-苯并五元环-苯基硫鎓盐及其衍生物。
实施例
为了更清楚地说明本公开，下面结合优选实施例对本公开做进一步的说明。本领域技术人员应当理解，下面所具体描述的内容是说明性的而非限制性的，不应以此限制本公开的保护范围。
实施例1：(4-(1H-茚-2-基)苯基)二甲基硫鎓盐-六氟磷酸盐((I)-1-PF6 -)
(a)中间体(4-(1H-茚-2-基)苯基)(甲基)硫醚的制备：将2-茚酮(10g，76mmol)的乙醚(50mL)滴加到(4-(甲硫基)苯基)溴化镁中，再回流一小时进行反应，反应完毕后，将混合物冷却后倒入NH4Cl水溶液(4.3g，80mmol，在20mL H2O中)进行萃取，得到醚层，用无水Na2SO4干燥后进行旋蒸。然后将残留物倒入H2SO4的溶液中(8mL)进行抽滤得到固体，用H2O彻底洗涤，在空气中干燥，然后进行重结晶(两次)或进行色谱分离得到目标产物(I)-a，产率87％。
(b)(4-(1H-茚-2-基)苯基)二甲基硫鎓-三氟甲磺酸盐:
在三口烧瓶中加入(I)-a，并加入50mLDCM进行溶解，然后在恒压滴液漏斗中加入1.1当量的三氟甲烷磺酸甲酯，然后给装置通入N2，冷却到-5℃，滴加三氟甲烷磺酸甲酯，滴加完成后缓慢恢复至室温进行搅拌反应12h，反应完成后用DCM萃取三次，分出有机相，用无水硫酸钠干燥，蒸去溶剂后用硅胶柱层析得到目标产物(I)-b，产率83％。
(c)(4-(1H-茚-2-基)苯基)二甲基硫鎓盐-六氟磷酸盐：
沉淀物(I)-b溶于适量丙酮中，逐滴加入六氟磷酸钾的水溶液(2当量)，抽滤析出的沉淀，再将沉淀溶解逐滴加入六氟磷酸钠水溶液(2当量)，重复三次后用水洗并干燥，得到目标化合物(I)-1-PF6 -，三步总产率43.61％。
实施例2：(4-(苯并呋喃-2-基)苯基)二甲基硫鎓六氟磷酸盐((I)-2-PF6 -)
(a)中间体2-(4-(甲硫基)苯基)苯并呋喃的制备：
中间体：在500mL的三口烧瓶中加入碳酸钠(30mmol)，茴香硫醚20mmol以及0.25mmol四(三苯基膦)钯，然后加入少量DMF(约5mL)，充入N2，将苯并呋喃-2-基硼酸(22mmol)溶于25mL的DMF后加入恒压滴液漏斗，将装置放入100℃的油浴中进行加热搅拌，加热约20min后，打开恒压滴液漏斗滴加硼酸取代的苯并呋喃的DMF溶液，滴加完后继续在100℃下加热搅拌反应，反应完全后，向混合溶液中加入DCM，充分混合后，用水萃取三遍，分出有机相，用无水硫酸钠干燥，蒸去溶剂后用硅胶柱层析得到目标产物(I)-a，得到黄色固体，产率：70％
(b)(4-(苯并呋喃-2-基)苯基)二甲基硫鎓三氟甲磺酸盐和(c)(4-(苯并呋喃-2-基)苯基)二甲基硫鎓盐-六氟磷酸盐的制备过程具体操作见实施例1，总产率47.82％。
实施例3：(4-(苯并[d]噻吩-2-基)苯基)二甲基硫鎓盐-六氟磷酸盐((I)-10-PF6 -)
(a)中间体2-(4-(甲硫基)苯基)苯并[d]噻唑
将ZnO NPs(10mg)、2-氨基苯硫醇(1mmol)和4-(甲硫基)苯甲醛(1mmol)加入到盛有少量乙醇(EtOH)的烧瓶中，在室温下进行搅拌反应，反应2-5min后(直到混合物凝固)，用薄层色谱法进行检测，确定反应完成后，将得到的固体分散在热乙醇中，用抽滤过滤除去催化剂ZnO NPs，取滤液，将滤液冷却至室温进行重结晶可得到纯结晶产物的(I)-a，产率89％。
(b)(4-(苯并[d]噻吩-2-基)苯基)二甲基硫鎓三氟甲磺酸盐和(c)(4-(苯并[d]噻吩-2-基)苯基)二甲基硫鎓六氟磷酸盐具体操作见实施例1，总产率61.13％。
实施例4：(4-(6-甲氧基苯并呋喃-2-基)苯基)二甲基硫鎓六氟磷酸盐((I)-13-PF6 -)
(a)中间体2-(2,2-二溴乙烯基)-5-甲氧基苯酚的制备
在500mL的三口烧瓶中加入PPh3(78mmol)，充入N2，再加入适量DCM，然后将容器冷却至0℃，再添加CBr4(39mmol)的DCM溶液。10min后，逐滴添加NEt3(78mmol)并搅拌5min，再逐滴添加2-羟基-4-甲氧基苯甲醛(13mmol)的DCM溶液，在0℃下搅拌30min后将其回复到室温并再反应60min，随后添加饱和NH4Cl水溶液来终止反应，再用DCM萃取。萃取后得到的有机层旋蒸后得到的物质在大量Et2O和少量乙醇中溶解，用水萃取后得到的有机层经旋转蒸发浓缩，用硅胶柱层析得到目标产物2-(2,2-二溴乙烯基)-5-甲氧基苯酚，产率72％。
(b)中间体2-溴-6-甲氧基苯并呋喃的制备：
向三口烧瓶中添加2-(2,2-二溴乙烯基)-5-甲氧基苯酚(3mmol)、CuI(0.15mmol)和K3PO4(6mmol)，充入N2，密封后加入THF，将其置于80℃的预热油浴中反应6h，将烧瓶从油浴中取出并冷却至室温。用大量的Et2O作为展开剂，在硅胶垫上对所得内容物进行过滤。所得溶液进行旋蒸浓缩，得到2-溴-6-甲氧基苯并呋喃，产率75％。
(c)中间体6-甲氧基-2-(4-(甲硫基)苯基)苯并呋喃的制备：
中间体(a)：在500mL的三口烧瓶中加入碳酸钠(30mmol)，2-溴-6-甲氧基苯并呋喃20mmol以及0.25mmol四(三苯基膦)钯，然后加入少量DMF(约5mL)，充入N2，将(4-(甲硫基)苯基)硼酸(22mmol)溶于25mL的DMF后加入恒压滴液漏斗，将装置放入100℃的油浴中进行加热搅拌，加热约20min后，打开恒压滴液漏斗滴加(4-(甲硫基)苯基)硼酸的DMF溶液，滴加完后继续在100℃下加热搅拌反应，反应完全后，向混合溶液中加入DCM，充分混合后，用水萃取三遍，分出有机相，用无水硫酸钠干燥，蒸去溶剂后用硅胶柱层析得到目标产物(I)-a，得到黄色固体，产率：50％-71％。
(b)(4-(6-甲氧基苯并呋喃-2-基)苯基)二甲基硫鎓三氟甲磺酸盐和(c)(4-(6-甲氧基苯并呋喃-2-基)苯基)二甲基硫鎓六氟磷酸盐：
具体操作见实施例1，总产率34.91％。
实施例5：其余硫鎓盐的制备及表征
其余各种二甲基硫鎓盐的中间体的制备除了原材料变化外，基本的方法都是一致的，这里不再重复。制备的三步总产率以及硫鎓盐的质谱数据如下表所示。
实施例6：(4-(苯并噻吩-2-基)苯基)苄基硫鎓六氟锑酸盐的制备((I)-35-SbF6 -)：
(a)中间体2-(4-(甲硫基)苯基)苯并噻吩的制备：
在500mL的三口烧瓶中加入碳酸钠(30mmol)，茴香硫醚20mmol以及0.25mmol四(三苯基膦)钯，然后加入少量DMF(约5mL)，充入N2，将苯并噻吩-2-基硼酸(22mmol)溶于25mL的DMF后加入恒压滴液漏斗，将装置放入100℃的油浴中进行加热搅拌，加热约20min后，打开恒压滴液漏斗滴加硼酸取代的苯并呋喃的DMF溶液，滴加完后继续在100℃下加热搅拌反应，反应完全后，向混合溶液中加入DCM，充分混合后，用水萃取三遍，分出有机相，用无水硫酸钠干燥，蒸去溶剂后用硅胶柱层析得到目标产物(I)-a，得到黄色固体，产率：70％
(b)(4-(苯并噻吩-2-基)苯基)苄基硫鎓盐-三氟甲磺酸盐：
在三口烧瓶中加入(I)-a(1当量)，抽真空除氧后加入50mL无水DCM进行溶解，在0℃冷浴中，搅拌下加入10当量的三氟甲磺酸，逐滴滴加用无水DCM释过的1.9当量甲酸苄酯，滴加完成后恢复至室温进行搅拌反应24h，用薄层色谱法进行检测，确定反应完成后用DCM稀释反应液后，搅拌下滴入碱液(氢氧化钠11当量，碳酸氢钠9当量)中和过量的酸，用DCM萃取三次，分出有机相，用无水硫酸钠干燥，蒸去溶剂后得到目标产物(I)-b。
(c)(4-(苯并噻吩-2-基)苯基)苄基硫鎓六氟锑酸盐的制备过程：
沉淀物(I)-b溶于适量丙酮中，逐滴加入六氟锑酸钠的水溶液(2当量)，抽滤析出的沉淀，再将沉淀溶解逐滴加入六氟锑酸钠水溶液(2当量)，重复三次后用水洗并干燥，得到目标化合物(I)-35-SbF6 -，总产率51.52％。
实施例7：(4-(苯并[d]恶唑-2-基)苯基)苄基硫鎓六氟锑酸盐((I)-43-SbF6 -)
(a)中间体2-(4-(甲硫基)苯基)苯并[d]恶唑的制备
将ZnO NPs(10mg)、2-氨基苯硫醇(1mmol)和4-(甲硫基)苯甲醛(1mmol)加入到盛有少量乙醇(EtOH)的烧瓶中，在室温下进行搅拌反应，反应2-5min后(直到混合物凝固)，用薄层色谱法进行检测，确定反应完成后，将得到的固体分散在热乙醇中，用抽滤过滤除去催化剂ZnO NPs，取滤液，将滤液冷却至室温进行重结晶可得到纯结晶产物的(I)-a，产率89％。
(b)(4-(苯并[d]恶唑-2-基)苯基)苄基硫鎓三氟甲磺酸盐和(c)(4-(苯并[d]恶唑-2-基)苯基)苄基硫鎓六氟锑酸盐具体见实施例6，总产率31.89％。
实施例8：(4-(萘[2,1-b]呋喃-2-基)苯基)苄基硫鎓盐-六氟锑酸盐((I)-74-SbF6 -)
(a)中间体2-溴萘并[2,1-b]呋喃
向三口烧瓶中添加1-(2,2-二溴乙烯基)萘-2-醇(1.0mmol)、CuI(0.15mmol)和Cs2CO3(0.50mmol)，充入N2，密封后加入EtOH(2mL)，将其置于80℃的预热油浴中反应8h，将烧瓶从油浴中取出并冷却至室温。用大量的Et2O作为展开剂，在硅胶垫上对所得内容物进行过滤。所得溶液进行旋蒸浓缩，得到2-溴萘并[2,1-b]呋喃，产率75％-95％。
(b)中间体2-(4-(甲硫基)苯基)萘并[2,1-b]呋喃
中间体：在500mL的三口烧瓶中加入碳酸钠(30mmol)，2-溴萘并[2,1-b]呋喃(20mmol)以及0.25mmol四三苯基膦钯，然后加入少量DMF(约5mL)，充入N2，将(4-(甲硫基)苯基)硼酸(22mmol)溶于25mL的DMF后加入恒压滴液漏斗，将装置放入100℃的油浴中进行加热搅拌，加热约20min后，打开恒压滴液漏斗滴加(4-(甲硫基)苯基)硼酸的DMF溶液，滴加完后继续在100℃下加热搅拌反应，反应完全后，向混合溶液中加入DCM，充分混合后，用水萃取三遍，分出有机相，用无水硫酸钠干燥，蒸去溶剂后用硅胶柱层析得到目标产物(I)-a，产率：75％。
(c)(4-(萘[2,1-b]呋喃-2-基)苯基)苄基硫鎓三氟甲磺酸盐和(d)(4-(萘[2,1-b]呋喃-2-基)苯基)苄基硫鎓六氟锑酸盐具体见实施例6，总产率45.59％。
实施例9：其余硫鎓六氟锑酸盐的制备及表征
其余各种苄基硫鎓盐的中间体的制备除了原材料变化外，基本的方法都是一致的，这里不再重复。制备的三步总产率以及硫鎓盐的质谱数据如下表所示。
实施例10：(I)-1-PF6 -～(I)-14-PF6 -的LED光固化实验以及涂料性质测试
含环氧基团样品体系按下列配方制作(以重量百分比计)
双功能团树脂(EPOX)：97％
光引发剂((I)-1-PF6 -～(I)-14-PF6 -)：3％
将上述配制实施例混合物涂覆于卡纸板上形成约25-30微米的涂层，以广州和光同盛科技有限公司生产的单位功率为1000mW/cm2的发射波长为365纳米的LED光源(3厘米宽和80厘米长LED面光源)为激发光源，放置于变速传送带。以指甲反复压刻刮擦不产生印迹为光聚合固化完成的判据。
结果表明含有本实施例的化合物均以高于25米/分钟的速度高效固化。
对上述通过光固化得到的涂层通过手摇铅笔硬度计进行硬度测试，测得其硬度为4H。
实施例11：((I)-33-SbF6 -～(I)-45-SbF6 -)的LED光固化实验以及涂料性质测试
含环氧基团样品体系按下列配方制作(以重量百分比计)
单功能团树脂(CHO)：98.5％
光引发剂((I)-33-SbF6 -～(I)-45-SbF6 -)：1.5％
将上述配制实施例混合物涂覆于卡纸板上形成约30-35微米的涂层，以广州和光同盛科技有限公司生产的单位功率为1000mW/cm2的发射波长为365纳米的LED光源(3厘米宽和80厘米长LED面光源)为激发光源，放置于变速传送带。以指甲反复压刻刮擦不产生印迹为光聚合固化完成的判据。
结果表明含有本实施例的化合物均以高于30米/分钟的速度高效固化。
对上述通过光固化得到的涂层通过手摇铅笔硬度计进行硬度测试，测得其硬度为4H。
上述对实施例的描述是为了便于该技术领域的普通技术人员能理解和使用本发明。熟悉本领域技术人员显然可以容易的对这些实施例做出各种修改，并把在此说明的一般原理应用到其他实施例中，而不必经过创造性的劳动。因此，本发明不限于上述实施例。本领域技术人员根据本发明的原理，不脱离本发明的范畴所做出的改进和修改都应该在本发明的保护范围之内。
Claims (3)
1.一种(4-(苯并[d]噻吩-2-基)苯基)二甲基硫鎓盐-六氟磷酸盐，其特征在于，其通式如下：
2.如权利要求1所述一种(4-(苯并[d]噻吩-2-基)苯基)二甲基硫鎓盐-六氟磷酸盐的制备方法，其特征在于，包括步骤(a)、步骤(b)、步骤(c)：
(a)中间体2-(4-(甲硫基)苯基)苯并[d]噻唑
将ZnO NPs 10mg、2-氨基苯硫醇1mmol和4-(甲硫基)苯甲醛1mmol加入到盛有少量乙醇(EtOH)的烧瓶中，在室温下进行搅拌反应，反应2-5min后(直到混合物凝固)，用薄层色谱法进行检测，确定反应完成后，将得到的固体分散在热乙醇中，用抽滤过滤除去催化剂ZnONPs，取滤液，将滤液冷却至室温进行重结晶可得到纯结晶产物的(I)-a，产率89％；
(b)(4-(1H-茚-2-基)苯基)二甲基硫鎓-三氟甲磺酸盐:
在三口烧瓶中加入(I)-a，并加入50mLDCM进行溶解，然后在恒压滴液漏斗中加入1.1当量的三氟甲烷磺酸甲酯，然后给装置通入N2，冷却到-5℃，滴加三氟甲烷磺酸甲酯，滴加完成后缓慢恢复至室温进行搅拌反应12h，反应完成后用DCM萃取三次，分出有机相，用无水硫酸钠干燥，蒸去溶剂后用硅胶柱层析得到目标产物(I)-b，产率83％，
(c)(4-(1H-茚-2-基)苯基)二甲基硫鎓盐-六氟磷酸盐：
沉淀物(I)-b溶于适量丙酮中，逐滴加入2当量六氟磷酸钾的水溶液，抽滤析出的沉淀，再将沉淀溶解逐滴加入2当量六氟磷酸钠水溶液，重复三次后用水洗并干燥，得到目标化合物(I)-1-PF6 -，三步总产率61.13％。
3.根据权利要求1所述的一种(4-(苯并[d]噻吩-2-基)苯基)二甲基硫鎓盐-六氟磷酸盐应用于LED光源的光引发剂。
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