Issue 5, 2013

Switching of emissive and NLO properties in push–pull chromophores with crescent PPV-like structures

Abstract

We report on a series of novel homologous push–pull compounds, in which identical donor (a dimethylamino) and acceptor (a malonate ester) functionalities endcap crescent PPV fragments, bearing, respectively, 1, 2 and 3 p-phenylenevinylene units in direct linear conjugation (compounds 7–9). The three compounds exhibit striking differences in their linear and nonlinear optical properties. The shorter compound 7 exhibits aggregation-induced emission with a strong luminescence in the solid state (blue emission, photoluminescence quantum yield 38%), and it is nonemissive in solution; the more extended conjugated systems 8 and 9 show classical aggregation-caused quenching in the solid state, while high quantum yield photoluminescence (21 and 93% in toluene) is restored in diluted solutions, through mechanisms involving intramolecular charge transfer in the excited states. EFISH measurements in solutions demonstrate a strong solvent and concentration dependence. As rationalized with the aid of molecular modelling, compounds 8 and, more markedly, 9 aggregate in stable centrosymmetric dimers in solution.

Graphical abstract: Switching of emissive and NLO properties in push–pull chromophores with crescent PPV-like structures

Supplementary files

Article information

Article type
Paper
Submitted
07 Sep 2012
Accepted
23 Nov 2012
First published
26 Nov 2012

Phys. Chem. Chem. Phys., 2013,15, 1666-1674

Switching of emissive and NLO properties in push–pull chromophores with crescent PPV-like structures

C. Coluccini, A. K. Sharma, M. Caricato, A. Sironi, E. Cariati, S. Righetto, E. Tordin, C. Botta, A. Forni and D. Pasini, Phys. Chem. Chem. Phys., 2013, 15, 1666 DOI: 10.1039/C2CP43140H

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