Bandrowski’s Base Revisited: Toward a Unprecedented Class of Quinonediimines or New Two-Way Chromophoric Molecular Switches
摘要:
Temperature-con trolled reactivity places Bandrowski's base 3 at the crossroads of a new versatile strategy for the preparation of two different categories of chromophores. We describe the access to a new class of quinonediimines (8) with an extended pi-conjugation owing to the presence of imine functions. Under slightly different conditions, Bandrowski's base appears to be the precursor of choice in the preparation of a novel pH- and liglit-dependent binary molecular switch. This molecule (11) is constituted of a benzobis(imidazole) core that can be reversibly protonated and a diarylethene unit which can be reversibly converted into its closed form upon irradiation. Triggered by two independent variables, 11 provides four distinct optical states for molecular number processing.
Bandrowski’s Base Revisited: Toward a Unprecedented Class of Quinonediimines or New Two-Way Chromophoric Molecular Switches
作者:Ekaterina A. Shilova、Arnault Heynderickx、Olivier Siri
DOI:10.1021/jo902437u
日期:2010.3.19
Temperature-con trolled reactivity places Bandrowski's base 3 at the crossroads of a new versatile strategy for the preparation of two different categories of chromophores. We describe the access to a new class of quinonediimines (8) with an extended pi-conjugation owing to the presence of imine functions. Under slightly different conditions, Bandrowski's base appears to be the precursor of choice in the preparation of a novel pH- and liglit-dependent binary molecular switch. This molecule (11) is constituted of a benzobis(imidazole) core that can be reversibly protonated and a diarylethene unit which can be reversibly converted into its closed form upon irradiation. Triggered by two independent variables, 11 provides four distinct optical states for molecular number processing.