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CN115322184A - 一种1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的制备方法 - Google Patents

一种1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的制备方法 Download PDF

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CN115322184A
CN115322184A CN202210781134.6A CN202210781134A CN115322184A CN 115322184 A CN115322184 A CN 115322184A CN 202210781134 A CN202210781134 A CN 202210781134A CN 115322184 A CN115322184 A CN 115322184A
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furyl
crystal
propylene
ketone
methylthienyl
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牟雪婷
曹丽凤
滕冰
钟德高
王田华
徐凯
陈睿
马金康
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Qingdao University
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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Abstract

本发明属于功能材料制备技术领域，涉及一种1‑(2‑呋喃基)‑3‑(4‑甲基噻吩基)‑2‑丙烯‑1‑酮晶体的制备方法，先将2‑乙酰呋喃与对甲硫基苯甲醛溶解在乙醇中并倒入烧杯搅拌后烘干，得到黄色固体；再将黄色固体完全溶解在甲醇中进行重结晶后将过滤掉杂质，最后采用自发成核法进行1‑(2‑呋喃基)‑3‑(4‑甲基噻吩基)‑2‑丙烯‑1‑酮晶体生长，制备的晶体纯度高，原料易得，制备方法简单，反应条件温和，生长周期短，生长出的晶体具有可高度极化的π电子共轭体系，利于产生较大的二阶非线性系数。

Description

一种1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的 制备方法
技术领域：
本发明属于功能材料制备技术领域，涉及一种1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的制备方法。
背景技术：
近年来，太赫兹(THz)技术的发展与应用成为国内外研究的热点之一，THz波产生、检测及应用等更是引起人们广泛的研究兴趣。THz波通常是指波长在0.03-3mm，频率在100GHz-10THz之间的电磁波段。近年来由于科学的发展和技术上的创新，新型THz材料等迅猛发展，出现了各种各样的THz波辐射源，如量子级联激光器、半导体天线以及基于非线性光学(NLO)效应的晶体等，虽然许多THz源只能辐射有限的THz波谱范围，但基于有机非线性晶体的THz辐射源却可以覆盖整个THz范围。目前，用于产生THz波的有机非线性晶体分为离子型和分子型两种，其中离子型晶体主要是通过晶体内部阴阳离子间的离子键相互连接，一般来说这类晶体都拥有比较高的熔点和沸点。而分子型晶体则是通过晶体内部分子之间的范德华力或氢键相互连接的，这类晶体不易潮解，晶体稳定性较高，有机非线性晶体其非线性系数高，介电系数小，电光系数大，在太赫兹波产生方面有十分重要的地位。
发明内容：
本发明的目的在于克服现有技术存在的问题，提供一种新型有机非线性晶体材料1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮的制备方法，制备的晶体二次谐波信号大约是KDP的18倍，且生长周期短。
为实现上述目的，本发明制备1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的具体过程包括以下步骤：
(1)按照摩尔比1:1分别量取2-乙酰呋喃与对甲硫基苯甲醛，溶解在30-50ml乙醇中，然后倒入烧杯，在室温条件下磁力搅拌后烘干，得到黄色固体；
(2)将步骤(1)中干燥好的黄色固体完全溶解在甲醇中，重结晶1～4次后将溶液抽滤，过滤掉不溶性杂质，得到1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体生长原料；
(3)采用自发成核法进行1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体生长，以甲醇做溶剂，配置浓度为2～4g/100ml的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮溶液，倒入育晶瓶中，将溶液保持40℃，稳定12～24h，然后以0.3～1℃/天的速率降温，10～30天后，得到1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体。
本发明制备的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体化学式为：C14H14O2S。
本发明与现有技术相比，制备的新型有机光学晶体材料1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮纯度高，原料易得，制备方法简单，反应条件温和，生长周期短，生长出的晶体具有可高度极化的π电子共轭体系，利于产生较大的二阶非线性系数。
附图说明
图1为本发明所述1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的制备工艺图。
图2为本发明制备的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体生长原料实物图。
图3为本发明制备的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的二次谐波效率图。
图4为本发明制备的-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的核磁共振氢谱图。
图5为本发明制备的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的XRD图。
具体实施方式：
下面通过实施例并结合附图对本发明作详细说明。
实施例：
本实施例制备1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的工艺步骤为：
(1)按照摩尔比1:1分别量取2-乙酰呋喃与对甲硫基苯甲醛，溶解在30ml乙醇中，然后倒入烧杯，室温条件下磁力搅拌，然后烘干，得到黄色固体；
(2)将步骤(1)中干燥好的黄色固体完全溶解在乙醇中，重结晶2次，然后将1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮溶液抽滤，过滤掉不溶性杂质，得到较高纯度的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体生长原料；
(3)采用自发成核法进行1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体生长，以乙醇做溶剂，配置浓度为2g/100ml的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮溶液，倒入育晶瓶中，将溶液保持40℃，稳定12h，然后以1℃/天的速率降温，10天后，得到1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体，其二次谐波效率图如图3所示，XRD图如图5所示。
本实施例将5mg制备的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮溶解于0.5ml氘代DMSO中，利用JNM ECP-600型核磁共振波谱仪做NMR1H谱检测，从NMR1H图谱(图4)中得到表1所示数据。
表1：
Figure BDA0003727772610000031

Claims (2)

1.一种1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的制备方法，其特征在于，具体过程如下：
(1)按照摩尔比1:1分别量取2-乙酰呋喃与对甲硫基苯甲醛，溶解在30-50ml乙醇中，然后倒入烧杯，在室温条件下磁力搅拌后烘干，得到黄色固体；
(2)将步骤(1)中干燥好的黄色固体完全溶解在甲醇中，重结晶1～4次后将溶液抽滤，过滤掉不溶性杂质，得到1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体生长原料；
(3)采用自发成核法进行1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体生长，以甲醇做溶剂，配置浓度为2～4g/100ml的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮溶液，倒入育晶瓶中，将溶液保持40℃，稳定12～24h，然后以0.3～1℃/天的速率降温，10～30天后，得到1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体。
2.根据权利要求1所述1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的制备方法，其特征在于，制备的1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体化学式为：C14H14O2S。
CN202210781134.6A 2022-07-04 2022-07-04 一种1-(2-呋喃基)-3-(4-甲基噻吩基)-2-丙烯-1-酮晶体的制备方法 Pending CN115322184A (zh)

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Citations (2)

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Publication number Priority date Publication date Assignee Title
US5100584A (en) * 1989-12-25 1992-03-31 Nippon Oil And Fats Co., Ltd. Non-linear optical device
CN112574110A (zh) * 2020-12-25 2021-03-30 同济大学 酰基取代吡唑啉硫鎓盐衍生物的制备及其应用

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5100584A (en) * 1989-12-25 1992-03-31 Nippon Oil And Fats Co., Ltd. Non-linear optical device
CN112574110A (zh) * 2020-12-25 2021-03-30 同济大学 酰基取代吡唑啉硫鎓盐衍生物的制备及其应用

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
KABLI, R. A.，等: "Synthesis of a New Series of Furyl and Thienyl Substituted Pyrazolines Starting with Furyl and Thienyl Chalcones.", 《 J. INDIAN CHEM. SOC.》, vol. 68, 31 December 1991 (1991-12-31), pages 47 - 51 *
SHIXIONG CHEN, 等: "Effects of C3-aromatic heterocycles on 1, 3, 5-triaryl-2-pyrazoline sulfonium salt photoacid generators as light-emitting diode-sensitive cationic photoinitiators", 《J. POLYM. SCI.》, vol. 59, 31 December 2021 (2021-12-31), pages 1899 - 1911 *
V. P. PERESADA，等: "AZACYCLOALKANES. 31. ARYLALKYLPYRROLO[I, 2-a]PYRAZINES AND THEIR EFFECTS ON ISCHEMIZED MYOCARDIUM", 《KHIMIKO-FARMATSEVTICHESKII ZHURNAL》, vol. 22, no. 10, 31 December 1988 (1988-12-31), pages 1193 - 1197 *

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