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Issue 21, 2016
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Boron difluoride formazanate copolymers with 9,9-di-n-hexylfluorene prepared by copper-catalyzed alkyne–azide cycloaddition chemistry

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Abstract

The synthesis and characterization of copolymers based on boron difluoride formazanate (BF2L) and 9,9-di-n-hexylfluorene (hex2Fl) units are described. A series of model compounds [(BF2L)-(hex2Fl), (hex2Fl)-(BF2L)-(hex2Fl), and (BF2L)-(hex2Fl)-(BF2L)] were also studied in order to fully understand the spectroscopic properties of the title copolymers [(BF2L)-(hex2Fl)]n. The model compounds and copolymers, which were synthesized by copper catalyzed alkyne–azide cycloaddition chemistry, exhibited high molar absorptivities (25 700–54 900 M−1 cm−1), large Stokes shifts (123–143 nm, 3590–3880 cm−1), and tunable electrochemical behaviour (Image ID:c6py00441e-t1.gifca. −0.75 V and Image ID:c6py00441e-t2.gifca. −1.86 V vs. ferrocene/ferrocenium). The low-energy wavelength of maximum absorption and emission of the model compounds red-shifted relative to the BF2L repeating unit by ca. 30 nm per triazole ring formed, to maximum values of 557 nm and 700 nm in DMF, respectively. The low-energy absorption and emission properties of the copolymer were consistent with the model compound bearing two triazole rings [(hex2Fl)-(BF2L)-(hex2Fl)] and were not dependent on copolymer molecular weight. However, the title copolymers may show promise as light-harvesting materials based on their thin-film optical band gap of 1.67 eV.

Graphical abstract: Boron difluoride formazanate copolymers with 9,9-di-n-hexylfluorene prepared by copper-catalyzed alkyne–azide cycloaddition chemistry

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Publication details

The article was received on 11 Mar 2016, accepted on 26 Apr 2016 and first published on 05 May 2016


Article type: Paper
DOI: 10.1039/C6PY00441E
Author version available: Download Author version (PDF)
Citation: Polym. Chem., 2016,7, 3589-3598
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    Boron difluoride formazanate copolymers with 9,9-di-n-hexylfluorene prepared by copper-catalyzed alkyne–azide cycloaddition chemistry

    S. M. Barbon and J. B. Gilroy, Polym. Chem., 2016, 7, 3589
    DOI: 10.1039/C6PY00441E

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