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Issue 40, 2011
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Efficient crystallization induced emissive materials based on a simple push–pull molecular structure

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Abstract

Solid state luminescent materials are the subject of ever growing interest both from a scientific and a technological point of view. Aggregation caused quenching (ACQ) processes however represent an obstacle to the development of most luminogens in the condensed phase. This is why particularly fascinating are those materials showing higher emission intensity in the solid state than in solution. Here we report on three 4-dialkylamino-2-benzylidene malonic acid dialkyl esters, very simple push–pull molecules, which are hardly emissive in solution and in the amorphous phase but become good emitters in the crystalline phase according to what has been indicated as crystallization induced emission (CIE). Thanks to combined emission and NMR spectroscopies at different temperatures on the prototype compound 4-dimethylamino-2-benzylidene malonic acid dimethyl ester in solution, we give full evidence that a restricted intramolecular rotation (RIR) phenomenon, in particular the hindered rotation around the aryl main axis of the compound, is at the origin of this behaviour. In addition, solid state photophysical and X-ray diffraction structural characterization allow us to identify J-dimeric interactions as responsible for the particularly intense emission of two of the three compounds. Moreover, by exploiting the compounds' acidochromic properties, applications in sensors and optoelectronics are envisaged.

Graphical abstract: Efficient crystallization induced emissive materials based on a simple push–pull molecular structure

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Publication details

The article was received on 12 Jul 2011, accepted on 25 Aug 2011 and first published on 13 Sep 2011


Article type: Paper
DOI: 10.1039/C1CP22267H
Citation: Phys. Chem. Chem. Phys., 2011,13, 18005-18014
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    Efficient crystallization induced emissive materials based on a simple push–pull molecular structure

    E. Cariati, V. Lanzeni, E. Tordin, R. Ugo, C. Botta, A. Giacometti Schieroni, A. Sironi and D. Pasini, Phys. Chem. Chem. Phys., 2011, 13, 18005
    DOI: 10.1039/C1CP22267H

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