Charge-Transfer Interactions in Organic Functional Materials
<p>Distance dependence of the calculated <b>(a)</b> local exciton (LE) and charge-transfer exciton (CTE) energies <b>(b)</b> exciton coupling (2V) and <b>(c)</b> interaction energies of the electron transfer (t<sub>e</sub>) and hole transfer (t<sub>h</sub>) of various polyene dimers, with N = 6 (black), 10 (blue), 20 (red), and 40 (green) based on the four-orbital CM model (model 2 in <a href="#materials-03-04214-f011" class="html-scheme">Scheme 1</a>) [<a href="#B46-materials-03-04214" class="html-bibr">46</a>]. (Note that although we provide a detail distance dependence data, the van der Waals radius of carbon is 1.7 Å). Reproduced with permission from American Chemical Society.</p> "> Figure 2
<p>Distance dependence of the two low-lying excited states of various polyene dimers, with N = 6 <b>(a)</b>, 10 <b>(b)</b>, 20 <b>(c)</b>, 40 <b>(d)</b> calculated by model 1 (black), model 2 (blue) and model 3 (red line). The insets show the evolution of the energy gap of the two transitions as a function of the intermolecular distance (calculated by model 1). For clarity the data calculated by model 3, we specify the exact values at 3.0 and 5.0 Å for N = 6 (S<sub>1</sub>:4.657 eV, 4.827 eV; S<sub>2</sub>:5.264 eV, 5.098 eV), 10 (S<sub>1</sub>:3.580 eV, 3.722 eV; S<sub>2</sub>:4.174 eV, 4.037 eV), 20 (S<sub>1</sub>:2.814 eV, 2.893 eV; S<sub>2</sub>:3.227 eV, 3.153 eV), 40 (S<sub>1</sub>:2.558 eV, 2.596 eV; S<sub>2</sub>:2.784 eV, 2.748 eV) [<a href="#B46-materials-03-04214" class="html-bibr">46</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 3
<p>Dependence of the CT wave function (percentage) of lowest excited-state (blue) and second excited-state (red) as a function of chain size, with interchain distance d = 3.6 Å (upper), 3.8 Å (middle), 4.0 Å (lower), calculated by the CM model [<a href="#B46-materials-03-04214" class="html-bibr">46</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 4
<p>Contour polts of the CT exciton (in percentage) as a function of interchain distance (x axis) and chain size (y axis) of the first (right) and second (left) excited states in polyene dimers calculated using model 1 [<a href="#B46-materials-03-04214" class="html-bibr">46</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 5
<p>Chain size dependence of the three low-lying excited states of polyene dimers with interchain distance of 3.8 Å (calculated by model 1).</p> "> Figure 6
<p>Dependence of the CT wave function (percentage) of lowest excited-state (blue) and second excited-state (red) for <b>(a)</b> PV<sub>n</sub> <b>(b)</b> T<sub>n</sub> and <b>(c)</b> P<sub>n</sub> systems as a function of chain size, with interchain distance d = 3.6 Å (upper), 3.8 Å (middle), 4.0 Å (lower), calculated by the CM model.</p> "> Figure 7
<p>Various truncated CM model for molecule <b>4</b> with different optimized geometries for AM1 geometry (blue) and DFT geometry (red) [<a href="#B47-materials-03-04214" class="html-bibr">47</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 8
<p>Orbital diagram for “through-space’’ and “through-bond’’ interaction in the class I/II cyclophandienes with C<sub>2</sub> symmetry element [<a href="#B47-materials-03-04214" class="html-bibr">47</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 9
<p>Hückel MO’s of the J-aggregated biphenylenes, their energies, perimeter labels, and the five singly excited configurations responsible for the S<sub>1</sub>, N<sub>1</sub>, N<sub>2</sub>, P<sub>1</sub>, and P<sub>2</sub> states. [<a href="#B51-materials-03-04214" class="html-bibr">51</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 10
<p>State correlation diagrams of biphenylene, H-aggregrated biphenylene dimer (d = 4 Å), and J-aggregrated biphenylene dimer (d = 4 Å). [<a href="#B51-materials-03-04214" class="html-bibr">51</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 11
<p>CM Hamiltonian matrix (model 1), truncated four-orbital CM model (model 2) and truncated CM model when CT transitions are omitted from the calculation (model 3) [<a href="#B46-materials-03-04214" class="html-bibr">46</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 12
<p>The truncated MIM model with symmetry constraint [<a href="#B47-materials-03-04214" class="html-bibr">47</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 13
<p>Energy diagram of the interactions between two ethylenes based on simple Hückel model [<a href="#B46-materials-03-04214" class="html-bibr">46</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 14
<p>Simplified configuration interactions in the excited state for a dimer based on four-orbital model. The definition of all symbols is described in <a href="#sec2-materials-03-04214" class="html-sec">Section 2</a>.</p> "> Figure 15
<p>Three types of dimeric cyclophandienes with various dihedral angles between chromophores and tethered double bonds [<a href="#B47-materials-03-04214" class="html-bibr">47</a>]. Reproduced with permission from American Chemical Society.</p> "> Figure 16
<p>Molecular structures of cyclophandiene <b>1-4</b> [<a href="#B47-materials-03-04214" class="html-bibr">47</a>]<b>.</b> Reproduced with permission from American Chemical Society.</p> ">
Abstract
:1. Introduction
2. Theoretical Models
2.1. Composite-molecule (Molecule-in-molecule) method
2.2. Truncated composite-molecule (Molecule-in-molecule) method
2.3. Computational methodology
3. Charge-Transfer Interactions in Organic Materials
3.1. Charge-transfer interactions in polyenes
N-site | Ε a | Ε b | CT% a | Major CT-state function a |
---|---|---|---|---|
6 | 4.40 (E1) | 4.40 (E1) | 35.0 | 0.42 HM1(M2) → LM2(M1) (100%)c |
4.91 (E2) | 4.91 (E2) | 69.9 | 0.59 H M1(M2) → L M2(M1) (99.6%) | |
10 | 3.38 (E1) | 3.38 (E1) | 29.1 | 0.38 H M1(M2) → L M2(M1) (99.2%) |
3.95 (E2) | 3.96 (E2) | 65.9 | 0.57 H M1(M2) → L M2(M1) (98.6%) | |
20 | 2.64 (E1) | 2.64 (E1) | 22.9 | 0.33 H M1(M2) → L M2(M1) (95.2%) |
3.17 (E2) | 3.17 (E2) | 10.5 | 0.22 H M1(M2) → L M2(M1) (92.2%) | |
30 | 2.46 (E1) | 2.46 (E1) | 20.9 | 0.29 H M1(M2) → L M2(M1) (80.4%) |
2.84 (E2) | 2.84 (E2) | 27.2 | 0.24 H-1 M1(M2) → L M2(M1), 0.25 H M1(M2) → L+1 M2(M1) (88.3%) | |
40 | 2.39 (E1) | 2.39 (E1) | 20.0 | 0.27 H M1(M2) → L M2(M1) (72.9%) |
2.62 (E2) | 2.62 (E2) | 23.9 | 0.22 H-1 M1(M2) → L M2(M1), 0.22 H M1(M2) → L+1 M2(M1) (81.0%) |
3.2. Charge-transfer interactions in OPV, OT and OP
Ε a | CT% | CT-State function HM1(M2)→LM2(M1) H-1 M1(M2)→L M2(M1)+ H M1(M2)→L++1 M2(M1) | ||
---|---|---|---|---|
PPV2 | 3.70 (E1) | 18.5 | 97.3% | |
4.15 (E2) | 8.8 | 100.0% | ||
PPV7 | 2.80 (E1) | 15.1 | 70.1% | |
3.02 (E2) | 17.4 | 83.0% | ||
TP3 | 2.70 (E1) | 21.2 | 96.6% | |
3.23 (E2) | 5.0 | 100.0% | ||
TP10 | 1.89 (E1) | 16.8 | 74.4% | |
2.17 (E2) | 20.3 | 82.9% | ||
PPP3 | 3.68 (E1) | 17.1 | 98.4% | |
4.08(E2) | 6.4 | 100.0% | ||
PPP10 | 3.07 (E1) | 13.8 | 70.1% | |
3.27 (E2) | 15.7 | 82.5% |
4. Charge-Transfer Interactions in Cyclophanes
Entry | num (opt) | no tether (CT %) | tether (CT %) | T-space : T-bond (%) |
---|---|---|---|---|
1 | 1 (AM1) a | 27.79 | 27.04 | 100 : 0 |
2 | 2 (AM1) a | 6.32 | 5.22 | 100 : 0 |
3 | 3 (AM1) a | 0.14 | 19.65 | 1 : 99 |
4 | 4 (AM1) a | 0.99 | 4.41 | 22 : 78 |
5 | 4 (DFT) a | 0.60 | 6.85 | 9 : 91 |
6 | 4 (AM1) b | 0.74 | 2.51 | 29 : 71 |
7 | 4 (DFT) b | 0.46 | 4.87 | 9 : 91 |
8 | 4 (AM1) c | 0.65 | 3.12 | 21 : 79 |
9 | 4 (DFT) c | 0.36 | 4.52 | 8 : 92 |
State | Ea | f | state function |
---|---|---|---|
1 | 26.96 | 0 | 0.69 + 0.15 |
2 | 27.46 | 0 | 0.70 |
3 | 31.02 | 0 | 0.69 + 0.12 |
4 | 31.71 | 0.19 | 0.70 |
5 | 36.67 | 0 | 0.70 |
6 | 37.09 | 0 | 0.69 + 0.15 |
7 | 40.24 | 0 | 0.52 + 0.44 + 0.18 |
8 | 41.19 | 0.03 | 0.70 |
9 | 42.33 | 0 | 0.54- 0.42- 0.14 |
10 | 42.76 | 0 | 0.68 - 0.19 |
11 | 43.54 | 0.22 | 0.70 + 0.11 |
12 | 45.15 | 3.60 | 0.66 - 0.24 |
State | E | f | state function |
---|---|---|---|
1 | 27.40 | 0 | 0.70 |
2 | 27.51 | 0 | 0.70 |
3 | 31.45 | 0 | 0.70 |
4 | 31.77 | 0.23 | 0.70 |
5 | 40.79 | 0 | 0.70 |
6 | 40.80 | 0 | 0.70 |
7 | 42.22 | 0 | 0.70 |
8 | 43.38 | 0.04 | 0.70 |
9 | 43.59 | 0 | 0.70 |
10 | 44.78 | 3.84 | 0.68 - 0.16 |
11 | 45.42 | 0 | 0.70 |
12 | 45.46 | 0.24 | 0.68 + 0.16 |
5. Synopsis
Acknowledgements
References and Notes
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Lin, H.-C.; Jin, B.-Y. Charge-Transfer Interactions in Organic Functional Materials. Materials 2010, 3, 4214-4251. https://doi.org/10.3390/ma3084214
Lin H-C, Jin B-Y. Charge-Transfer Interactions in Organic Functional Materials. Materials. 2010; 3(8):4214-4251. https://doi.org/10.3390/ma3084214
Chicago/Turabian StyleLin, Hsin-Chieh, and Bih-Yaw Jin. 2010. "Charge-Transfer Interactions in Organic Functional Materials" Materials 3, no. 8: 4214-4251. https://doi.org/10.3390/ma3084214