Issue 15, 2011

Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band

Abstract

Non-concerted [2+2] and [4+2] cycloadditions between N,N-dimethylanilino-substituted 1,1,2,4,4-pentacyanobuta-1,3-diene and 4-ethynyl-N,N-dimethylaniline are controlled by solvent polarity and provide access to a highly functionalised 6,6-dicyanopentafulvene featuring an intense, low-energy charge-transfer band and to an unusual spirocyclic zwitterion, characterised by X-ray analysis.

Graphical abstract: Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band

Supplementary files

Article information

Article type
Communication
Submitted
13 Jan 2011
Accepted
22 Feb 2011
First published
11 Mar 2011

Chem. Commun., 2011,47, 4520-4522

Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band

G. Jayamurugan, J. Gisselbrecht, C. Boudon, F. Schoenebeck, W. B. Schweizer, B. Bernet and F. Diederich, Chem. Commun., 2011, 47, 4520 DOI: 10.1039/C1CC10247H

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