Self-assembly of 1,3,5-benzenetricarboxylic (trimesic) acid and its analogues

Sergei V. Kolotuchin, Paul A. Thiessen, Edward E. Fenlon, Scott R. Wilson, Colin J. Loweth, Steven C. Zimmerman

Research output: Contribution to journalArticlepeer-review

131 Scopus citations

Abstract

A crystalline inclusion complex between 1,3,5-benzenetricarboxylic acid (trimesic acid, 1) and pyrene was grown from diethyl ether/ethanol and its structure was determined by X-ray analysis. Trialkyltrimesic acids 4b-4e were synthesized in seven steps from 1,3,5-trichlorobenzene (5). Trimethyltrimesic acid (4a) was synthesized in four steps from mesitylene. All five substituted trimesic acids were crystallized to determine their potential as clathrate hosts and to compare their solid-state structures with the parent trimesic acid. The X-ray structures of 4a-4d were resolved and are reported. A covalent analogue of a trimesic acid dimer (13) was synthesized in seven steps from 2-butylisophthalic acid and its solid-state structure determined.

Original languageEnglish
Pages (from-to)2537-2547
Number of pages11
JournalChemistry - A European Journal
Volume5
Issue number9
DOIs
StatePublished - 1 Jan 1999
Externally publishedYes

Keywords

  • Crystal engineering
  • Hydrogen bonds
  • Self-assembly
  • Solid-state structures
  • Trimesic acid

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Organic Chemistry

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