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Title: Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes

Abstract

Seven three-ring phenylene-ethynylene (PE) structural analogs, differing only in the lengths of alkyl chains on terminal aniline substituents, show 50–62 nm bathochromic shifts in emission maxima in response to mechanical force (mechanofluorochromism, MC). These shifts are fully reversible with heat or solvent fuming. Shearing of these solids yields a transition from green-emitting crystalline phases to orange-emitting amorphous phases as established by differential scanning calorimetry and X-ray diffraction. Molecules with shorter alkyl chain lengths required higher temperatures to recover the hypsochromically shifted crystalline phases after grinding, while the recovery with chain lengths longer than butyl occurred at room temperature. In addition to this structure-dependent thermochromism, these compounds retain their MC properties in polymer hosts to various extents. The crystalline phases of these materials have PE chromophores that are twisted due to non-covalent perfluoroarene–arene (ArF–ArH) interactions involving perfluorophenyl pendants and the terminal rings of the PE chromophore, resulting in interrupted conjugation and an absence of chromophore aggregation. The MC behavior of an analog without the perfluoroarene rings is severely attenuated. This work demonstrates the general utility of twisted PEs as stimuli-responsive moieties and reveals clear structure–property relationships regarding the effects of alkyl chain length on these materials.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [1];  [1];  [1];  [2]; ORCiD logo [1]
  1. Department of Chemistry, Tufts University, Medford, USA
  2. Department of Chemical & Biomolecular Engineering, University of Connecticut, USA
Publication Date:
Research Org.:
Tufts University, Boston, MA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1439913
Alternate Identifier(s):
OSTI ID: 1505082
Grant/Contract Number:  
SC0016423
Resource Type:
Published Article
Journal Name:
Chemical Science
Additional Journal Information:
Journal Name: Chemical Science Journal Volume: 9 Journal Issue: 24; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United Kingdom
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE

Citation Formats

Sharber, Seth A., Shih, Kuo-Chih, Mann, Arielle, Frausto, Fanny, Haas, Terry E., Nieh, Mu-Ping, and Thomas, Samuel W. Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes. United Kingdom: N. p., 2018. Web. doi:10.1039/C8SC00980E.
Sharber, Seth A., Shih, Kuo-Chih, Mann, Arielle, Frausto, Fanny, Haas, Terry E., Nieh, Mu-Ping, & Thomas, Samuel W. Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes. United Kingdom. doi:10.1039/C8SC00980E.
Sharber, Seth A., Shih, Kuo-Chih, Mann, Arielle, Frausto, Fanny, Haas, Terry E., Nieh, Mu-Ping, and Thomas, Samuel W. Mon . "Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes". United Kingdom. doi:10.1039/C8SC00980E.
@article{osti_1439913,
title = {Reversible mechanofluorochromism of aniline-terminated phenylene ethynylenes},
author = {Sharber, Seth A. and Shih, Kuo-Chih and Mann, Arielle and Frausto, Fanny and Haas, Terry E. and Nieh, Mu-Ping and Thomas, Samuel W.},
abstractNote = {Seven three-ring phenylene-ethynylene (PE) structural analogs, differing only in the lengths of alkyl chains on terminal aniline substituents, show 50–62 nm bathochromic shifts in emission maxima in response to mechanical force (mechanofluorochromism, MC). These shifts are fully reversible with heat or solvent fuming. Shearing of these solids yields a transition from green-emitting crystalline phases to orange-emitting amorphous phases as established by differential scanning calorimetry and X-ray diffraction. Molecules with shorter alkyl chain lengths required higher temperatures to recover the hypsochromically shifted crystalline phases after grinding, while the recovery with chain lengths longer than butyl occurred at room temperature. In addition to this structure-dependent thermochromism, these compounds retain their MC properties in polymer hosts to various extents. The crystalline phases of these materials have PE chromophores that are twisted due to non-covalent perfluoroarene–arene (ArF–ArH) interactions involving perfluorophenyl pendants and the terminal rings of the PE chromophore, resulting in interrupted conjugation and an absence of chromophore aggregation. The MC behavior of an analog without the perfluoroarene rings is severely attenuated. This work demonstrates the general utility of twisted PEs as stimuli-responsive moieties and reveals clear structure–property relationships regarding the effects of alkyl chain length on these materials.},
doi = {10.1039/C8SC00980E},
journal = {Chemical Science},
number = 24,
volume = 9,
place = {United Kingdom},
year = {2018},
month = {1}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1039/C8SC00980E

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Cited by: 7 works
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Figures / Tables:

Figure 1 Figure 1: Chemical structure and example mechanofluorochromic response of aniline terminated three-ring phenylene-ethynylenes.

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    New cationic Ir( iii ) complexes without “any soft substituents”: aggregation-induced emission and piezochromic luminescence
    journal, January 2018

    • Wang, Yue; Yang, Tianzhi; Liu, Xingman
    • Journal of Materials Chemistry C, Vol. 6, Issue 45
    • DOI: 10.1039/c8tc04512g

    Directed polymorphism and mechanofluorochromism of conjugated materials through weak non-covalent control
    journal, January 2019

    • Sharber, Seth A.; Mann, Arielle; Shih, Kuo-Chih
    • Journal of Materials Chemistry C, Vol. 7, Issue 27
    • DOI: 10.1039/c9tc01301f

    Strategic modification of ligands for remarkable piezochromic luminescence (PCL) based on a neutral Ir( iii ) phosphor
    journal, January 2019

    • Li, Dan; Li, Guangfu; Xie, Jiaxin
    • Journal of Materials Chemistry C, Vol. 7, Issue 35
    • DOI: 10.1039/c9tc03646f