Enabling Racemization of Axially Chiral Subphthalocyanine-Tetracyanobutadiene-Aniline Enantiomers by Triplet State Photogeneration

被引：16

作者：

Lavarda, Giulia ^{[1
]}

Bhattacharjee, Nicholus ^{[4
,5
]}

Brancato, Giuseppe ^{[4
,5
]}

Torres, Tomas ^{[1
,2
,3
]}

Bottari, Giovanni ^{[1
,2
,3
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, Campus Cantoblanco, Madrid 28049, Spain

[2] IMDEA Nanociencia, C Faraday 9,Campus Cantoblanco, Madrid 28049, Spain

[3] Univ Autonoma Madrid, Inst Adv Res Chem Sci IAdChem, Madrid 28049, Spain

[4] Scuola Normale Super Pisa, Piazza Cavalieri 7, I-56126 Pisa, Italy

[5] Ist Nazl Fis Nucl, Largo Pontecorvo 3, I-56100 Pisa, Italy

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 47期

关键词：

atropisomer; photoracemization; subphthalocyanine; tetracyano-1; 3-butadiene; triplet state; PHOTORACEMIZATION; PHOTOLYSIS;

D O I：

10.1002/anie.202010133

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In recent years, several tetracyanobuta-1,3-diene (TCBD) conjugates have been prepared by linking the tetracyano unit to various electroactive moieties. These push-pull conjugates, besides showing interesting physicochemical properties, are axially chiral, a feature arising from the restricted rotation around the central bond of the butadiene. Yet, only in a few cases, separation and isolation of the enantiomers have been successfully achieved, owing to the configurational lability of the corresponding enantiopure species. Herein, we report the first example of photo- and electroactive TCBD-based derivatives showing unprecedented configurational stability and a peculiar light-triggered enantiomer conversion mechanism enabled by triple-state photogeneration. These systems represent a nice addition to the fast-increasing arsenal of artificial, light-controllable molecular switches.

引用

页码：21224 / 21229

页数：6