Cycloaddition reactions of polyenic donor-π-acceptor systems with an electron-rich alkyne: access to new chromophores with second-order optical nonlinearities

Elena Galán; Raquel Andreu; Javier Garín; Jesús Orduna; Belén Villacampa; Beatriz E Diosdado

doi:10.1039/c2ob26515j

Cycloaddition reactions of polyenic donor-π-acceptor systems with an electron-rich alkyne: access to new chromophores with second-order optical nonlinearities

Org Biomol Chem. 2012 Nov 21;10(43):8684-91. doi: 10.1039/c2ob26515j.

Authors

Elena Galán¹, Raquel Andreu, Javier Garín, Jesús Orduna, Belén Villacampa, Beatriz E Diosdado

Affiliation

¹ Departamento de Química Orgánica, ICMA, Universidad de Zaragoza-CSIC, 50009 Zaragoza, Spain.

PMID: 23034533
DOI: 10.1039/c2ob26515j

Abstract

The formal [2 + 2] cycloaddition-cycloreversion (CA-CR) between 4-ethynyl-N,N-dimethylaniline and polyenic Donor-π-Acceptor (D-π-A) systems takes place to yield compounds bearing two donors and one acceptor. Structural, linear and second-order nonlinear optical (NLO) properties of the new molecules reveal the stronger polarization of these systems when compared to analogous merocyanines lacking the dimethylaminophenyl (DMA) ring.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Cyclization
Electrons
Models, Molecular
Molecular Structure
Polyenes / chemistry*

Substances

Alkynes
Polyenes