Benzene-1,3,5-tricarboxamide n-alkyl ester and carboxylic acid derivatives: tuneable structural, morphological and thermal properties

Lynes, Amy D.; Hawes, Chris S.; Ward, Edward N.; Haffner, Benjamin; Möbius, Matthias E.; Byrne, Kevin; Schmitt, Wolfgang; Pal, Robert; Gunnlaugsson, Thorfinnur

Abstract

A family of five benzene-1,3,5-tricarboxamide (BTA) compounds with varied side arm functionality [alkyl: n = 3, 4 and 5 chains; and ester and carboyxic acids] is reported. Investigations into their self-assembly behaviour revealed the extent to which minor changes in the side arm functionality can affect the structures formed. The carboxylic acid derivatives have a tendency to form gels, while the ester derivatives instead form crystalline phases with associated thermotropic phase transitions. The influence of the side chain length and terminal functional group is rationalised by a combination of single crystal X-ray diffraction studies and examinations of the bulk material properties.

Citation

Lynes, A. D., Hawes, C. S., Ward, E. N., Haffner, B., Möbius, M. E., Byrne, K., …Gunnlaugsson, T. (in press). Benzene-1,3,5-tricarboxamide n-alkyl ester and carboxylic acid derivatives: tuneable structural, morphological and thermal properties. CrystEngComm, 19(10), 1427-1438. https://doi.org/10.1039/c7ce00206h

• Journal Article Type: Article
• Acceptance Date: Feb 10, 2017
• Online Publication Date: Feb 10, 2017
• Deposit Date: Jun 14, 2023
• Journal: CrystEngComm
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 19
• Issue: 10
• Pages: 1427-1438
• DOI: https://doi.org/10.1039/c7ce00206h
• Keywords: Condensed Matter Physics; General Materials Science; General Chemistry
• Additional Information: : This document is CrossCheck deposited; : Supplementary Information; : Crystal Structure Data; : Chris S. Hawes (ORCID); : Edward N. Ward (ORCID); : Edward N. Ward (ResearcherID); : Matthias E. Möbius (ORCID); : Matthias E. Möbius (ResearcherID); : Wolfgang Schmitt (ORCID); : Thorfinnur Gunnlaugsson (ORCID); : The Royal Society of Chemistry has an exclusive publication licence for this journal; : Received 27 January 2017; Accepted 10 February 2017; Accepted Manuscript published 10 February 2017; Advance Article published 20 February 2017; Version of Record published 6 March 2017