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

共 32 条

[1]

[Anonymous], 2019, Angew. Chem, DOI DOI 10.1002/ANGE.201809984

[2] H/D solvent isotope effects on the photoracemization reaction of enantiomeric the tris(2,2′-bipyridine)ruthenium(ii) complex and its analogues [J].

Asahara, Masahiro ;

Kurimoto, Haruhiko ;

Nakamizu, Masato ;

Hattori, Shingo ;

Shinozaki, Kazuteru .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2020, 22 (11) :6361-6369

[3] Enantioenrichment of racemic BINOL by way of excited state proton transfer [J].

Ayad, Suliman ;

Posey, Victoria ;

Das, Anjan ;

Montgomery, Jason M. ;

Hanson, Kenneth .

CHEMICAL COMMUNICATIONS, 2019, 55 (09) :1263-1266

[4] Mechanistic Studies in Photocatalysis [J].

Buzzetti, Luca ;

Crisenza, Giacomo E. M. ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) :3730-3747

[5] Design of Collective Motions from Synthetic Molecular Switches, Rotors, and Motors [J].

Dattler, Damien ;

Fuks, Gad ;

Heiser, Joakim ;

Moulin, Emilie ;

Perrot, Alexis ;

Yao, Xuyang ;

Giuseppone, Nicolas .

CHEMICAL REVIEWS, 2020, 120 (01) :310-433

[6] Photosensitized singlet oxygen and its applications [J].

DeRosa, MC ;

Crutchley, RJ .

COORDINATION CHEMISTRY REVIEWS, 2002, 233 :351-371

[7] Artificial Photosynthesis at Efficiencies Greatly Exceeding That of Natural Photosynthesis [J].

Dogutan, Dilek K. ;

Nocera, Daniel G. .

ACCOUNTS OF CHEMICAL RESEARCH, 2019, 52 (11) :3143-3148

[8] A Key Factor Dominating the Competition between Photolysis and Photoracemization of [Ru(bipy)3]2+ and [Ru(phen)3]2+ Complexes [J].

Feng, Lixia ;

Wang, Yuekui .

INORGANIC CHEMISTRY, 2018, 57 (15) :8994-9001

[9] LASER PHOTOLYSIS STUDY OF PHOTORACEMIZATION OF 1,1'-BINAPHTHYL [J].

IRIE, M ;

YOSHIDA, K ;

HAYASHI, K .

JOURNAL OF PHYSICAL CHEMISTRY, 1977, 81 (10) :969-972

[10] Selective Cycloaddition of Tetracyanoethene (TCNE) and 7,7,8,8-Tetracyano-p-quinodimethane (TCNQ) to Afford meso-Substituted Phenylethynyl Porphyrins [J].

Koszelewski, Dominik ;

Nowak-Krol, Agnieszka ;

Gryko, Daniel T. .

CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (08) :1887-1894

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