A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis
2.2. NMR Spectroscopy
2.3. Photophysical Properties
Compounds | UV-vis absorption | Egopt (eV) | PL | Electrochemical data | |||
---|---|---|---|---|---|---|---|
λmax (nm) | λedge (nm) | λmax (nm) | Eonset (V) | EHOMO (eV) | ELUMO (eV) | ||
TTP | 359 | 386 | 3.21 | 426 | 1.12 | −5.84 | −2.63 |
THTP | 362 | 400 | 3.10 | 412 | 0.96 | −5.68 | −2.58 |
THTP-C | 344 | 433 | 2.86 | 443 | 0.92 | −5.64 | −2.78 |
2.4. Electrochemical Properties
2.5. X-ray Crystallographic Analysis
Emprical formula | C64H78S4 |
Formula weight | 975.50 |
Space group | C2/c |
a [Å] | 33.829(3) |
b [Å] | 19.9281(17) |
c [Å] | 18.3660(15) |
α [˚] | 90.00 |
β [˚] | 113.6410(10) |
γ [˚] | 90.00 |
V [Å3] | 11342.4(16) |
Z | 8 |
Dcalcd. [g cm−3] | 1.143 |
θ range | 2.38-25.02 |
index ranges | −32 ≤ h ≤ 40 − 23≤ k ≤ 18 – 20 ≤ l ≤ 21 |
R1, wR2∗ [I > 2σ(I)] | 0.0889; 0.3567 |
GOF | 1.073 |
S(1)-C(1) | 1.734(7) | C(5)-C(11) | 1.479(8) |
S(1)-C(4) | 1.737(6) | C(6)-C(7) | 1.452(8) |
S(2)-C(7) | 1.734(6) | C(6)-C(18) | 1.468(8) |
S(2)-C(10) | 1.736(8) | C(7)-C(8) | 1.394(8) |
S(3)-C(32) | 1.733(7) | C(8)-C(9) | 1.422(9) |
S(3)-C(29) | 1.745(7) | C(9)-C(10) | 1.355(10) |
S(4)-C(25) | 1.734(7) | C(10)-C(39) | 1.507(11) |
S(4)-C(27) | 1.744(7) | C(11)-C(12) | 1.380(8) |
C(1)-C(2) | 1.346(9) | C(11)-C(16) | 1.407(8) |
C(1)-C(33) | 1.504(8) | C(12)-C(13) | 1.387(8) |
C(2)-C(3) | 1.425(8) | C(13)-C(14) | 1.388(8) |
C(2)-H(2) | 0.9300 | C(13)-C(57) | 1.539(9) |
C(3)-C(4) | 1.388(8) | C(14)-C(15) | 1.395(8) |
C(3)-C(8) | 1.409(8) | C(15)-C(16) | 1.413(8) |
C(4)-C(5) | 1.436(8) | C(15)-C(24) | 1.471(8) |
C(5)-C(6) | 1.395(8) | C(16)-C(17) | 1.433(8) |
C(18)-C(19) | 1.387(8) | C(17)-C(22) | 1.422(8) |
C(19)-C(20) | 1.384(8) | C(17)-C(18) | 1.422(8) |
C(20)-C(21) | 1.389(9) | C(23)-C(24) | 1.393(8) |
C(21)-C(22) | 1.388(8) | C(23)-C(29) | 1.444(8) |
C(22)-C(23) | 1.478(8) | C(24)-C(25) | 1.438(8) |
C(1)-S(1)-C(4) | 92.3(3) | C(4)-C(3)-C(8) | 119.2(5) |
C(7)-S(2)-C(10) | 92.5(3) | C(4)-C(3)-C(2) | 112.6(6) |
C(32)-S(3)-C(29) | 92.9(3) | C(8)-C(3)-C(2) | 128.2(6) |
C(25)-S(4)-C(27) | 92.0(3) | C(3)-C(4)-C(5) | 121.8(5) |
C(2)-C(1)-C(33) | 129.2(6) | C(3)-C(4)-S(1) | 110.0(4) |
C(2)-C(1)-S(1) | 111.3(5) | C(5)-C(4)-S(1) | 128.1(4) |
C(33)-C(1)-S(1) | 119.5(5) | C(6)-C(5)-C(4) | 119.5(5) |
C(1)-C(2)-C(3) | 113.8(6) | C(6)-C(5)-C(11) | 119.0(5) |
C(1)-C(2)-H(2) | 123.1 | C(4)-C(5)-C(11) | 121.5(5) |
C(8)-C(7)-S(2) | 109.6(5) | C(5)-C(6)-C(7) | 118.0(5) |
C(6)-C(7)-S(2) | 129.1(5) | C(5)-C(6)-C(18) | 120.1(5) |
C(7)-C(8)-C(3) | 120.1(5) | C(7)-C(6)-C(18) | 121.8(5) |
C(7)-C(8)-C(9) | 113.6(6) | C(8)-C(7)-C(6) | 121.3(5) |
C(3)-C(8)-C(9) | 126.3(6) | C(9)-C(10)-C(39) | 129.9(8) |
C(10)-C(9)-C(8) | 112.9(6) | C(9)-C(10)-S(2) | 111.5(5) |
C(12)-C(13)-C(14) | 117.2(5) | C(39)-C(10)-S(2) | 118.5(7) |
C(12)-C(13)-C(57) | 119.7(5) | C(12)-C(11)-C(16) | 118.7(5) |
C(14)-C(13)-C(57) | 123.0(5) | C(12)-C(11)-C(5) | 123.4(5) |
3. Experimental
3.1. General
3.2. Synthesis
4. Conclusions
Acknowledgements
References and Notes
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Duan, Z.-F.; Huang, X.-Q.; Yang, Z.-G.; Hoshino, D.; Kitanaka, S.; Zhao, G.-Y.; Nishioka, Y. A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties. Molecules 2011, 16, 4467-4481. https://doi.org/10.3390/molecules16064467
Duan Z-F, Huang X-Q, Yang Z-G, Hoshino D, Kitanaka S, Zhao G-Y, Nishioka Y. A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties. Molecules. 2011; 16(6):4467-4481. https://doi.org/10.3390/molecules16064467
Chicago/Turabian StyleDuan, Zong-Fan, Xian-Qiang Huang, Zhi-Gang Yang, Daiki Hoshino, Susumu Kitanaka, Gao-Yang Zhao, and Yasushiro Nishioka. 2011. "A Novel Thiophene-Fused Polycyclic Aromatic with a Tetracene Core: Synthesis, Characterization, Optical and Electrochemical Properties" Molecules 16, no. 6: 4467-4481. https://doi.org/10.3390/molecules16064467