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Unusual Mechanohypsochromic Luminescence and Unique Bidirectional Thermofluorochromism of Long-Alkylated Simple DPP Dyes

Abstract

There have been hundreds of organic and metallorganic compounds found to exhibit mechanobathochromic luminescence within tens of nanometers. This paper presents the first example of unusual mechanohypsochromic luminescence and unique bidirectional thermofluorochromism based on 1,4-diketo-2,5-di(tetradecyl)-3,6-bis-(4-chlorophenyl)pyrrolo[3,4-c]pyrrole (TDPP). Pristine TDPP powder is a red emitting crystal (645 nm, R state) and can be changed into a yellow amorphous state (544 nm, Y state) by mechanical grinding or solution spin-coating. The Y state could revert to R state upon annealing below 60 oC or solvent-fuming, however, annealing the Y state above 70 oC produces a new green-emitting crystalline state (523 nm, G state). Moreover, the G state can transform to Y and R states upon grinding and solvent-fuming, respectively. In contrast, those novel phenomena are not observed in the butylated DPP, demonstrating that peripheral alkyl chain lengths of organic fluorophores can play the diverse functional role in determining the solid-state aggregation behavior and fluorescence properties. This work has enriched kinds of stimuli responsive materials and developed new optical properties of alkylated DPPs.

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Publication details

The article was received on 05 Apr 2017, accepted on 09 May 2017 and first published on 12 May 2017


Article type: Paper
DOI: 10.1039/C7TC01453H
Citation: J. Mater. Chem. C, 2017, Accepted Manuscript
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    Unusual Mechanohypsochromic Luminescence and Unique Bidirectional Thermofluorochromism of Long-Alkylated Simple DPP Dyes

    S. Ying, M. Chen, Z. Liu, M. Zheng, H. Zhang, S. Xue and W. Yang, J. Mater. Chem. C, 2017, Accepted Manuscript , DOI: 10.1039/C7TC01453H

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