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Fluorescent organic single crystals with elastic bending flexibility: 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene derivatives.

ABSTRACT: Organic single crystals with elastic bending flexibility are rare because they are generally brittle. We report here fluorescent organic single crystals based on thiophene-tetrafluorobenzene-thiophene derivatives, mainly 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene. Three derivatives were synthesized by Pd-catalyzed cross-coupling reactions (Stille or direct arylation pathways). The crystallization of the derivatives gave large (mm- or cm-scale) crystals. Two crystals of 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene, 1, and 1,4-bis(4-methylthien-2-yl)-2,3,5,6-tetrafluorobenzene, 3, bent under applied stress and quickly recovered its original shape upon relaxation. The other crystal of 1,4-bis(5-methylthien-2-yl)-2,3,5,6-tetrafluorobenzene, 2, showed brittle breakage under applied stress (normal behavior). Fibril lamella crystal structure based on criss-cross packed slip-stacked molecular wires and its structural integrity are important factors for the design and production of next generation crystal materials with elastic bending flexibility. Furthermore, mechanical bending-relaxation resulted in reversible change of the morphology and fluorescence (mechanofluorochromism). Such bendable crystals would lead to the next generation solid-state fluorescent and/or semiconducting materials.

SUBMITTER: Hayashi S

PROVIDER: S-EPMC5573333 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Fluorescent organic single crystals with elastic bending flexibility: 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene derivatives.

Hayashi Shotaro S Asano Atsushi A Kamiya Natsumi N Yokomori Yoshinobu Y Maeda Takuto T Koizumi Toshio T

Scientific reports 20170825 1

Organic single crystals with elastic bending flexibility are rare because they are generally brittle. We report here fluorescent organic single crystals based on thiophene-tetrafluorobenzene-thiophene derivatives, mainly 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene. Three derivatives were synthesized by Pd-catalyzed cross-coupling reactions (Stille or direct arylation pathways). The crystallization of the derivatives gave large (mm- or cm-scale) crystals. Two crystals of 1,4-bis(thien-2-yl)-2, ...[more]

PMID: 28842693

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Project description:Although many examples of mechanically flexible crystals are currently known, their utility in all-flexible devices is not yet adequately demonstrated, despite their immense potential for fabricating high performance flexible devices. Here, we report two alkylated diketopyrrolopyrrole (DPP) semiconducting single crystals, one of which displays impressive elastic mechanical flexibility whilst the other is brittle. Using the single crystal structures and density functional theory (DFT) calculations, we show that the methylated diketopyrrolopyrrole (DPP-diMe) crystals, with dominant π-stacking interactions and large contributions from dispersive interactions, are superior in terms of their stress tolerance and field-effect mobility (μ FET) when compared to the brittle crystals of the ethylated diketopyrrolopyrrole derivative (DPP-diEt). Periodic dispersion-corrected DFT calculations revealed that upon the application of 3% uniaxial strain along the crystal growth (a)-axis, the elastically flexible DPP-diMe crystal displays a soft energy barrier of only 0.23 kJ mol-1 while the brittle DPP-diEt crystal displays a significantly larger energy barrier of 3.42 kJ mol-1, in both cases relative to the energy of the strain-free crystal. Such energy-structure-function correlations are currently lacking in the growing literature on mechanically compliant molecular crystals and have the potential to support a deeper understanding of the mechanism of mechanical bending. The field effect transistors (FETs) made of flexible substrates using elastic microcrystals of DPP-diMe retained μ FET (from 0.019 cm2 V-1 s-1 to 0.014 cm2 V-1 s-1) more efficiently even after 40 bending cycles when compared to the brittle microcrystals of DPP-diEt which showed a significant drop in μ FET just after 10 bending cycles. Our results not only provide valuable insights into the bending mechanism, but also demonstrate the untapped potential of mechanically flexible semiconducting crystals for designing all flexible durable field-effect transistor devices.

Dataset Information

Fluorescent organic single crystals with elastic bending flexibility: 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene derivatives.

Publications

Fluorescent organic single crystals with elastic bending flexibility: 1,4-bis(thien-2-yl)-2,3,5,6-tetrafluorobenzene derivatives.

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