Regioselective synthesis of 5-monostyryl and 2-tetracyanobutadiene BODIPY dyes. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2011

Regioselective synthesis of 5-monostyryl and 2-tetracyanobutadiene BODIPY dyes.

Songlin Niu
  • Fonction : Auteur
Gilles Ulrich
Raymond Ziessel
  • Fonction : Auteur

Résumé

Several unsymmetrically 2,5-disubstituted BODIPY dyes were obtained from 2-substituted derivatives (iodo, ethynylaryl) using a regioselective Knoevenagel condensation reaction with dimethylaminobenzaldehyde. The unsaturated, unsymmetrical 2-ethynyl-5-styryl-BODIPY undergoes a regioselective [2 + 2] cycloaddition reaction with tetracyanoethylene leading to the 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) derivative. This shows rich redox activity with two reversible oxidation and three reversible reduction waves at +0.72 V, +1.04 V; -0.32 V, -0.78 V, and -1.50 V, respectively.

Domaines

Chimie organique
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Dates et versions

hal-00649283 , version 1 (07-12-2011)

Identifiants

Citer

Songlin Niu, Gilles Ulrich, Pascal Retailleau, Raymond Ziessel. Regioselective synthesis of 5-monostyryl and 2-tetracyanobutadiene BODIPY dyes.. Organic Letters, 2011, 13 (19), pp.4996-4999. ⟨10.1021/ol201600s⟩. ⟨hal-00649283⟩
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