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

doi:10.1002/(SICI)1521-3765(19990903)5:9<2537::AID-CHEM2537>3.0.CO;2-3

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 journal › Article › peer-review

132 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 language	English
Pages (from-to)	2537-2547
Number of pages	11
Journal	Chemistry - A European Journal
Volume	5
Issue number	9
DOIs	https://doi.org/10.1002/(SICI)1521-3765(19990903)5:9<2537::AID-CHEM2537>3.0.CO;2-3
State	Published - 1 Jan 1999
Externally published	Yes

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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10.1002/(SICI)1521-3765(19990903)5:9<2537::AID-CHEM2537>3.0.CO;2-3

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title = "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 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.",

keywords = "Crystal engineering, Hydrogen bonds, Self-assembly, Solid-state structures, Trimesic acid",

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T1 - Self-assembly of 1,3,5-benzenetricarboxylic (trimesic) acid and its analogues

AU - Kolotuchin, Sergei V.

AU - Thiessen, Paul A.

AU - Fenlon, Edward E.

AU - Wilson, Scott R.

AU - Loweth, Colin J.

AU - Zimmerman, Steven C.

PY - 1999/1/1

Y1 - 1999/1/1

N2 - 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.

AB - 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.

KW - Crystal engineering

KW - Hydrogen bonds

KW - Self-assembly

KW - Solid-state structures

KW - Trimesic acid

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DO - 10.1002/(SICI)1521-3765(19990903)5:9<2537::AID-CHEM2537>3.0.CO;2-3

M3 - Article

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SN - 0947-6539

VL - 5

SP - 2537

EP - 2547

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 9

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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