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Issue 9, 2017
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Controlling solid-state optical properties of stimuli responsive dimethylamino-substituted dibenzoylmethane materials

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Abstract

The mechanochromic luminescent (ML) properties of boron coordinated β-diketones (BF2bdks) have been widely studied, however the stimuli responsive properties of uncoordinated β-diketones (bdks) are less known. While bdk dyes show promising properties, including high contrast ML, rapid room temperature self-erasure, solvatochromism, and aggregation induced emission (AIE), previously reported dyes exhibit emission over a narrow range of wavelengths (∼420–500 nm). To tune luminescence over a broader color range, dimethylamino (DMA) substituted β-diketones were synthesized with a series of electron donating and withdrawing substituents. Solvatochromism, aggregation induced emission (AIE), ML, and thermochromism were investigated. Most dyes showed positive solvatochromic shifts and were responsive to mechanical and thermal stimuli. The solid-state emission wavelengths correlated with the electron withdrawing strength of the para substituent and ranged from blue to orange (488–578 nm). Structural and thermal characterization was performed by powder X-ray diffraction (XRD) and differential scanning calorimetry (DSC) respectively. These data indicate that stimuli responsive properties are the result of a crystalline to amorphous phase transition. Additionally, the aggregation induced emission (AIE) properties of iodo and cyano substituted dyes were measured in THF/H2O solutions. Both showed intense emission resulting from aggregation. The sensitivity of these dyes toward matrix polarity was further investigated by fabricating polystyrene films with increasing concentrations of dye and camphoric anhydride, a non-emissive polar dopant. A red-shift in emission was observed in these films which demonstrated that matrix effects can be used to tune the emission of DMA-substituted diketones.

Graphical abstract: Controlling solid-state optical properties of stimuli responsive dimethylamino-substituted dibenzoylmethane materials

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Publication details

The article was received on 07 Apr 2017, accepted on 27 Apr 2017 and first published on 11 May 2017


Article type: Research Article
DOI: 10.1039/C7QM00157F
Citation: Mater. Chem. Front., 2017,1, 1804-1817
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    Controlling solid-state optical properties of stimuli responsive dimethylamino-substituted dibenzoylmethane materials

    T. Butler, F. Wang, M. Sabat and C. L. Fraser, Mater. Chem. Front., 2017, 1, 1804
    DOI: 10.1039/C7QM00157F

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