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.

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

Bhattacharjee N.;Brancato G.
;
Bottari G.
2020

Abstract

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.
2020
Settore CHIM/02 - Chimica Fisica
atropisomer; photoracemization; subphthalocyanine; tetracyano-1,3-butadiene; triplet state
File in questo prodotto:
File Dimensione Formato  
202010133.pdf

Accesso chiuso

Tipologia: Published version
Licenza: Non pubblico
Dimensione 1.57 MB
Formato Adobe PDF
1.57 MB Adobe PDF   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11384/101576
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 15
  • ???jsp.display-item.citation.isi??? 14
  • OpenAlex ND
social impact