<scp>π‐Extension</scp> of Isoindigos (<scp>IIDs</scp>) through C—H/N—H Activation and Alkyne Annulation<sup>†</sup>-Reference-Cited by-同舟云学术

π‐Extension of Isoindigos (IIDs) through C—H/N—H Activation and Alkyne Annulation^†

Published:2023-07-06 Issue:20 Volume:41 Page:2589-2596
ISSN:1001-604X
Container-title:Chinese Journal of Chemistry
language:en
Short-container-title:Chin. J. Chem.

Author:

Wang Kang¹,Chen Liangliang²,Huang Yan‐Ying²³,Qin Liyuan²³,Li Cheng²,Zhang Xi‐Sha²³⁴,Luo Feixian⁵,Duan Zheng¹,Zhang Guanxin²,Zhang Deqing²³

Affiliation:

1. College of Chemistry, Green Catalysis Center Zhengzhou University Zhengzhou Henan 450000 China

2. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic Solids, Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China

3. University of Chinese Academy of Sciences Beijing 100049 China

4. State Key Laboratory of Applied Organic Chemistry Lanzhou University Lanzhou Gansu 730000 China

5. Key Laboratory of Ecology and Environment in Minority Areas Minzu University of China, National Ethnic Affairs Commission Beijing 100081 China

Abstract

Comprehensive SummaryIsoindigo (IID) is widely used as organic dye and conjugated unit in opto‐electronic materials. Functionalization of IID to increase its structural complexity is demanding for obtaining diversity properties. Herein, we developed a direct C—H/N—H activation method of IIDs via double alkyne annulations and synthesized π‐extended IIDs with two pairs of 5/7 membered rings. The structure of the π‐extended IIDs was characterized and confirmed by 1H NMR, 13C NMR, HRMS and X ray crystal analysis. Their physical properties were characterized by UV‐vis absorption, cyclic voltammetry and thermogravimetric analysis. The absorption coefficient of the annulated products enhanced significantly compared with the non‐annulated analogue.

Funder

National Natural Science Foundation of China

Youth Innovation Promotion Association of the Chinese Academy of Sciences

Publisher

Wiley

Subject

General Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/cjoc.202300149

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