Synthesis and organogelating behaviour of amino acid-functionalised triphenylenes

Meegan, Jonathan E.; Yang, Xiaofei; Rungsirisakun, Ratana; Cosgrove, Sebastian C.; Bushby, Richard J.; Sadeghpour, Amin; Rappolt, Michael; Brydson, Rik; Ansell, Richard J.

Abstract

Four novel amino acid-functionalised triphenylenes have been prepared with glycine, L-alanine, L-phenylalanine and L-tryptophan ethyl ester side-chains. The glycine derivative is a good gelator of chloroform, the alanine derivative gels ethanol and toluene, and the phenylalanine derivative gels benzene and toluene. The tryptophan derivative does not gel any of the solvents tested, most probably due to its more bulky structure, but forms microspheres by evaporation-induced self-assembly. The self-assembly properties of the π-gelators have been investigated using infrared, UV-absorption and fluorescence spectroscopy, concentration- and temperature-dependent NMR, and X-ray scattering experiments on dried xerogel as well as the wet organogel. The latter experiments suggest the glycine gel in chloroform includes columnar aggregates, with an overall disordered columnar oblique mesophase. These compounds are of interest because of the well-known hole-transporting properties of triphenylene liquid crystals: 1-D columnar assemblies of these compounds may find applications in organic electronic devices.

Citation

Meegan, J. E., Yang, X., Rungsirisakun, R., Cosgrove, S. C., Bushby, R. J., Sadeghpour, A., …Ansell, R. J. (in press). Synthesis and organogelating behaviour of amino acid-functionalised triphenylenes. Soft Matter, 13(35), 5922-5932. https://doi.org/10.1039/c7sm00676d

• Journal Article Type: Article
• Acceptance Date: Jul 26, 2017
• Online Publication Date: Jul 26, 2017
• Deposit Date: Jun 16, 2023
• Journal: Soft Matter
• Print ISSN: 1744-683X
• Electronic ISSN: 1744-6848
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 13
• Issue: 35
• Pages: 5922-5932
• DOI: https://doi.org/10.1039/c7sm00676d
• Keywords: Condensed Matter Physics; General Chemistry
• Additional Information: : This document is CrossCheck deposited; : Supplementary Information; : Sebastian C. Cosgrove (ORCID); : Michael Rappolt (ORCID); : Richard J. Ansell (ORCID); : The Royal Society of Chemistry has an exclusive publication licence for this journal; : Received 4 April 2017; Accepted 26 July 2017; Accepted Manuscript published 26 July 2017; Advance Article published 3 August 2017; Version of Record published 13 September 2017