p-Extension of Isoindigos (IIDs) through C-H/N-H Activation and Alkyne Annulation^&DAG;

Kang Wang,Liangliang Chen,Yan-Ying Huang,Liyuan Qin,Cheng Li,Xi-Sha Zhang,Feixian Luo,Zheng Duan,Guanxin Zhang,Deqing Zhang

CHINESE JOURNAL OF CHEMISTRY（2023）

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摘要

Isoindigo (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 p-extended IIDs with two pairs of 5/7 membered rings. The structure of the p-extended IIDs was characterized and confirmed by H-1 NMR, C-13 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.

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关键词

Isoindigo, C-H/N-H activation, Alkyne annulation, Opto-electronic function, Synthetic methods, Functionalized Units

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p-Extension of Isoindigos (IIDs) through C-H/N-H Activation and Alkyne Annulation&DAG;

p-Extension of Isoindigos (IIDs) through C-H/N-H Activation and Alkyne Annulation^&DAG;