Tuning the HOMO-LUMO gap of donor-substituted benzothiazoles

被引：37

作者：

Gautam, Prabhat ^{[1
]}

Maragani, Ramesh ^{[1
]}

Misra, Rajneesh ^{[1
]}

机构：

[1] Indian Inst Technol Indore, Dept Chem, Indore 452017, Madhya Pradesh, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 50期

关键词：

Donor acceptor; Benzothiazole; Click chemistry; Photophysical; Electrochemical; FERROCENYL BODIPYS SYNTHESIS; CHARGE-TRANSFER; BENZOTHIADIAZOLES SYNTHESIS; ACCEPTOR; CHROMOPHORES; DERIVATIVES; SYSTEMS; DESIGN; DYES; THIAZOLOTHIAZOLE;

D O I：

10.1016/j.tetlet.2014.10.094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of push-pull benzothiazoles were designed and synthesized by the Pd-catalyzed Sonogashira cross-coupling and [2+2] cycloaddition-retroelectrocyclization reactions. The photonic and electrochemical properties of these systems exhibit strong donor-acceptor interaction. The BTs 5-8 show strong intramolecular charge-transfer in the near-infrared (NIR) region. The absorption studies indicate systematic lowering of the optical HOMO-LUMO gap with increase in acceptor strength. The computational studies reveal that incorporation of strong acceptors TCNE and TCNQ results in substantial stabilization of the LUMO level compared to the HOMO level, leading to the low HOMO-LUMO gap and bathochromic shift of the absorption spectrum. The TCBD and DCNQ linked BTs 5-8 exhibit multi-step redox waves and improved thermal stability. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6827 / 6830

页数：4

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