4,7-二溴苯并[d][1,2,3]噻二唑和二氢吲哚供体用于染料敏化太阳能电池的新型DA-π-A1型有机敏化剂,Molecules

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4,7-二溴苯并[d][1,2,3]噻二唑和二氢吲哚供体用于染料敏化太阳能电池的新型DA-π-A1型有机敏化剂
Molecules ( IF 4.2 ) Pub Date : 2022-06-29 , DOI: 10.3390/molecules27134197
Nikita S Gudim ₁ , Ekaterina A Knyazeva _{1,

2} , Ludmila V Mikhalchenko ₁ , Maksim S Mikhailov ₂ , Lu Zhang ₃ , Neil Robertson ₃ , Oleg A Rakitin ₁

Affiliation

KEA系列的两种新型 DA-π-A1 无金属有机染料，含有苯并[ d ][1,2,3]噻二唑 (isoВТ) 内部受体，与环戊烷或环己烷环稠合的二氢吲哚供体 (D)，噻吩为合成了π-间隔物和作为锚定部分的氰基丙烯酸酯。4,7-二溴苯并[ d ]的单芳基化][1,2,3]噻二唑通过 Suzuki-Miyamura 交叉偶联反应表明，在二氢吲哚和咔唑供体的情况下，反应是非选择性的，即在每种情况下分离出两个单取代衍生物，而只有一个单取代β-异构体与苯基-和2-噻吩基硼酸形成。这可以通过以下事实来解释：与噻吩和苯相比，杂环二氢吲哚和咔唑片段是更强的供体基团，正如循环伏安法测量和计算二氢吲哚、咔唑、噻吩和苯分子的 HOMO 能量所证实的那样。单芳基(杂芳基)衍生物的结构经核磁共振光谱和X射线衍射严格证明。观察到KEA的光学和光伏特性染料表明，这些化合物有望用于制造太阳能电池。与对称苯并[ c ][1,2,3]噻二唑染料WS-2和MAX114的比较表明，苯并[ d ][1,2,3]噻二唑KEA染料的不对称性质导致 ICT 的深变色带与相应的苯并[ c ][1,2,5]噻二唑异构体进行比较。KEA染料具有 1.5–1.6 eV 的窄 HOMO-LUMO 间隙。在这些染料中，KEA321的功率效率（PCE）最好，为 5.17%，优于相应的对称苯并[ c ][1,2,3]噻二唑染料WS-2和MAX114 (5.07 和 4.90%)。

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Novel D-A-π-A1 Type Organic Sensitizers from 4,7-Dibromobenzo[d][1,2,3]thiadiazole and Indoline Donors for Dye-Sensitized Solar Cells

Two novel D-A-π-A1 metal-free organic dyes of the KEA series containing benzo[d][1,2,3]thiadiazole (isoВТ) internal acceptor, indoline donors fused with cyclopentane or cyclohexane rings (D), a thiophene as a π-spacer, and a cyanoacrylate as an anchor part were synthesized. Monoarylation of 4,7-dibromobenzo[d][1,2,3]thiadiazole by Suzuki-Miyamura cross-coupling reaction showed that in the case of indoline and carbazole donors, the reaction was non-selective, i.e., two monosubstituted derivatives were isolated in each case, whereas only one mono-isomer was formed with phenyl- and 2-thienylboronic acids. This was explained by the fact that heterocyclic indoline and carbazole fragments are much stronger donor groups compared to thiophene and benzene, as confirmed by cyclic voltammetry measurements and calculation of HOMO energies of indoline, carbazole, thiophene and benzene molecules. The structure of monoaryl(hetaryl) derivatives was strictly proven by NMR spectroscopy and X-ray diffraction. The optical and photovoltaic properties observed for the KEA dyes showed that these compounds are promising for the creation of solar cells. A comparison with symmetrical benzo[c][1,2,3]thiadiazole dyes WS-2 and MAX114 showed that the asymmetric nature of benzo[d][1,2,3]thiadiazole KEA dyes leads to a hypsochromic shift of the ICT band in comparison with the corresponding benzo[c][1,2,5]thiadiazole isomers. KEA dyes have a narrow HOMO-LUMO gap of 1.5–1.6 eV. Amongst these dyes, KEA321 recorded the best power efficiency (PCE), i.e., 5.17%, which is superior to the corresponding symmetrical benzo[c][1,2,3]thiadiazole dyes WS-2 and MAX114 (5.07 and 4.90%).

更新日期：2022-06-29

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