Self-Assembly of 1,3,5-Benzenetricarboxylic (Trimesic) Acid and Its Analogues

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 4 b ± 4 e were synthesized in seven steps from 1,3,5-trichlorobenzene (5). Trimethyltrimesic acid (4 a) 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 solidstate structures with the parent trimesic acid. The X-ray structures of 4 a ± 4 d 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.

Mastering fundamentals of supramolecular design with carboxylic acids. Common lessons from X-ray crystallography and scanning tunneling microscopy

“…5 An appropriate substitution of the building-blocks can 'decorate' the chicken-wire cavities creating a chiral environment, 31 introducing favorable interactions with guest molecules 32 or even blocking them completely. 33 Lowering the rigidity of the building block can cause either a random disorder, a uniform distortion or even form 1D structures as was seen in the cases of 31-33 (section 2.2.3).…”

Packing Similarities and Synthon Variabilities in Aminopyridinium Sulfoisophthalates

“…[49][50][51][52][53][54][55][56][57] However, in the presence of water molecules or amines the carboxylic group can form different type of hydrogen-bonding motifs and extended synthons. [58][59][60][61] A preferable acid⋯base heterosynthon is formed in multicomponent complexes (co-crystal, salts and their solvates). A special attention has been devoted to the hydrogen bonded assemblies of trimesic acid (TMA) with respect to formation of organic channel structures 64 as well as layered organic materials.…”

Self-assembling Dimeric and Trimeric Aggregates Based on Solvophobic and Charge-pairing Interactions

“…With increasing concentrations a trimer is also observed ðm=z ¼ 1483Þ: There is also a concentration-dependent monomer -dimer distribution below 1 mM, which confirms the specific formation of dimers, as opposed to nonspecific aggregation during the mass spectral determination. A similar study with 1,3,5-tris(hydroxymethyl)mesitylene (THM) [30], lacking the appended thiophenyl substituents, did not result in the formation of any defined aggregates of THM at a variety of concentrations (see Supplementary Material). Therefore, 3 clearly dimerizes, most likely through thiophenyl interactions.…”