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Organogels composed of trifluoromethyl anthryl cyanostyrenes: enhanced emission and self-assembly

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Abstract

A series of α-cyanostyrenes bearing anthracene and electron withdrawing trifluoromethyl units were designed and synthesized. The α-cyanostyrene skeleton favors aggregation induced enhanced emission behavior due to the restriction of intramolecular rotations. Remarkably, the anthryl cyanostyrenes bearing simple trifluoromethyl (CF3) substituents form stable organogels with enhanced fluorescence emission compared to their solution state. In water, the CF3 substituted anthrylstyrenes self-assemble into entangled fibrous nano/microstructures through intermolecular H-bonding, π–π stacking and cyano substituent interactions. The morphological features of the aggregates and the gels were substantiated using scanning electron microscopy, TEM, and powder XRD measurements. The stability of the gels was assessed using rheology investigations.

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Acknowledgements

Board of Research in Nuclear Sciences [37(2)/14/05/2016] for the financial grant, the NIIST Thiruvananthapuram for TEM measurements, and IIT Gandhinagar for overall infrastructural support.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Technology Gandhinagar, Palaj, Gandhinagar, 382355, India

    Jagadish Katla, Akshay J. M. Nair & Sriram Kanvah

  2. Department of Biological Engineering, Indian Institute of Technology Gandhinagar, Palaj, Gandhinagar, 382355, India

    Abhijeet Ojha

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  1. Jagadish Katla
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Correspondence to Sriram Kanvah.

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Katla, J., Nair, A.J.M., Ojha, A. et al. Organogels composed of trifluoromethyl anthryl cyanostyrenes: enhanced emission and self-assembly. Photochem Photobiol Sci 17, 395–403 (2018). https://doi.org/10.1039/c7pp00362e

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