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基于三苯胺-甲川菁的 D1-A1-π-A2/A3-D2 生色团体系：合成、光电及理论研究。

Triphenylamine-Merocyanine-Based D1-A1-π-A2/A3-D2 Chromophore System: Synthesis, Optoelectronic, and Theoretical Studies.

机构信息

Polymers and Functional Materials Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.

出版信息

Int J Mol Sci. 2019 Apr 1;20(7):1621. doi: 10.3390/ijms20071621.

DOI:10.3390/ijms20071621
PMID:30939780
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6479914/
Abstract

donor⁻acceptorDonor⁻acceptor⁻π⁻acceptor⁻donor (D1-A1-π-A2/A3-D2)-type small molecules, such TPA-MC-2 and TPA-MC-3, were designed and synthesized starting from donor-substituted alkynes (TPA-MC-1) via [2 + 2] cycloaddition-retroelectrocyclization reaction with tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) units, respectively. TPA-MC-2 and TPA-MC-3 chromophores differ on the A2/A3 acceptor subunit, which is 1,1,4,4-tetracyanobutadiene (TCBD) and a dicyanoquinodicyanomethane (DCQDCM), respectively. Both the derivative bearing same donors D1 (triphenylamine) and D2 (trimethylindolinm) and also same A1 (monocyano) as an acceptor, tetracyano with an aryl rings as the π-bridging moiety. The incorporation of TCNE and TCNQ as strong electron withdrawing units led to strong intramolecular charge-transfer (ICT) interactions, resulting in lower LUMO energy levels. Comparative UV⁻Vis absorption, fluorescence emission, and electrochemical and computational studies were performed to understand the effects of the TCNE and TCNQ subunits incorporated on TPA-MC-2 and TPA-MC-3, respectively.

摘要

供体-受体-π-受体-供体(D1-A1-π-A2/A3-D2)-型小分子，如 TPA-MC-2 和 TPA-MC-3，是从供体取代的炔烃(TPA-MC-1)通过[2+2]环加成-反电环化反应与四氰乙烯(TCNE)和 7,7,8,8-四氰醌二甲烷(TCNQ)单元分别合成的。TPA-MC-2 和 TPA-MC-3 发色团在 A2/A3 受体亚基上有所不同，分别为 1,1,4,4-四氰基丁二烯(TCBD)和二氰醌二氰甲烷(DCQDCM)。这两种衍生物都具有相同的供体 D1(三苯胺)和 D2(三甲基吲哚啉)以及相同的 A1(单氰基)作为受体，用芳环作为π桥接部分。引入 TCNE 和 TCNQ 作为强吸电子单元导致强烈的分子内电荷转移(ICT)相互作用，从而降低了 LUMO 能级。进行了比较的 UV-vis 吸收、荧光发射、电化学和计算研究，以了解 TCNE 和 TCNQ 亚基对 TPA-MC-2 和 TPA-MC-3 的影响。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/a04b2f97cc90/ijms-20-01621-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/19448760ed17/ijms-20-01621-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/70836753a08c/ijms-20-01621-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/a582f6e7a8c2/ijms-20-01621-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/950e02a81f3e/ijms-20-01621-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/bcd90248936c/ijms-20-01621-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/da866b01ff4b/ijms-20-01621-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/a04b2f97cc90/ijms-20-01621-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/19448760ed17/ijms-20-01621-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/70836753a08c/ijms-20-01621-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/a582f6e7a8c2/ijms-20-01621-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/950e02a81f3e/ijms-20-01621-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/bcd90248936c/ijms-20-01621-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/da866b01ff4b/ijms-20-01621-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/61a6/6479914/a04b2f97cc90/ijms-20-01621-g005.jpg

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