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

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.