Title: Sidechain engineering in anthracene derivatives: towards photofunctional liquid crystals

Authors: Lia C. Van Den Kerkhof; Kathryn M. Allan; Kathryn M. McGrath; John L. Spencer; Justin M. Hodgkiss

Addresses: MacDiarmid Institute for Advanced Materials and Nanotechnology, P.O. Box 600, Wellington, New Zealand; School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand ' MacDiarmid Institute for Advanced Materials and Nanotechnology, P.O. Box 600, Wellington, New Zealand; School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand ' MacDiarmid Institute for Advanced Materials and Nanotechnology, P.O. Box 600, Wellington, New Zealand; School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand ' MacDiarmid Institute for Advanced Materials and Nanotechnology, P.O. Box 600, Wellington, New Zealand; School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand ' MacDiarmid Institute for Advanced Materials and Nanotechnology, P.O. Box 600, Wellington, New Zealand; School of Chemical and Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand

Abstract: A series of anthracene derivatives were synthesised to explore how their sidechain configurations influenced their phase behaviour and thereby guiding the design of photofunctional liquid crystalline materials. In the case of 9,10-diphenylanthracene derivatives, longer and more alkyl sidechains resulted in lower melting temperatures, yet liquid crystallinity was not observed. A novel room-temperature molecular liquid was synthesised based on 9,10-diphenylanthracene, the optical properties of which may be exploited in photonic applications. Liquid crystallinity was observed in one of the derivatives of 9,10-bis(phenylethynyl)anthracene, forming a nematic phase at around 210°C. These results highlight the potential opportunities for photofunctional materials with enhanced properties if liquid crystalline anthracenes can be found with lower phase transition temperatures.

Keywords: photofunctional liquid crystals; 9,10-diphenylanthracene; DPA; 9,10-bis(phenylethynyl)anthracene; BPEA; molecular liquid; photon upconversion; sidechain engineering; anthracene derivatives; optical properties; photonics.

DOI: 10.1504/IJNT.2017.082463

International Journal of Nanotechnology, 2017 Vol.14 No.1/2/3/4/5/6, pp.432 - 445

Published online: 21 Feb 2017 *

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