β-Isoindigo-azaDIPYs: Fully Conjugated Hybrid Systems with Broad Absorption in the Visible Region

Angew Chem Int Ed Engl. 2021 May 25;60(22):12304-12307. doi: 10.1002/anie.202100888. Epub 2021 Apr 20.

Abstract

A one-step synthetic pathway for the preparation of fully conjugated β-isoindigo-azaDIPY hybrid chromophores comprised of β-isoindigo and azadipyrromethene moieties is reported. The target compounds were characterized by spectroscopic, crystallographic, and theoretical methods and show unprecedented broad absorption across the visible region of the electromagnetic spectrum. The X-ray crystal structure of the octa(n-butyl)-β-isoindigo-azaDIPY derivative revealed that a trans-configuration of the β-isoindigo fragment accompanies a planar conjugated core.

Keywords: 1-imino-3-thioisoindolines; BODIPY; density functional calculations; fused-ring systems; β-isoindigo.