Journal article
Crystal Engineering of Multiple Supramolecular Heterosynthons in Cocrystals of Boronic Acids: Structures, Photoreactivities, and Catalysis
Crystal growth & design, Vol.25(1), pp.38-52
01/01/2025
DOI: 10.1021/acs.cgd.4c01218
Abstract
Cocrystallizations of four para-substituted arylboronic acids, namely, 4-carboxyphenylboronic acid (4-cpba), 4-aminophenylboronic acid (4-apba), 4-aminocarbonylphenylboronic acid (4-acpba), and 4-nitrophenylboronic acid (4-npba), with trans-1,2-bis(4-pyridyl)ethylene (bpe) afforded seven multicomponent crystals, i.e., [(4-cpba)2(bpe)3], [(4-apba)2(bpe)3], [(4-acpba)2(bpe)], [(4-apba)(bpe)2(H 2 O)2], [(4-acpba)(bpe)2(H 2 O)2], [(4-cpbhme)(bpe)], and [(4-npbhme)2(bpe)], with the last two containing the hemimethyl ester (hme) of 4-cpba and 4-npba, respectively. SCXRD analyses reveal (B)O-H<middle dot><middle dot><middle dot>Npyr hydrogen bonds among the boronic acid (or hme) and bpe molecules. With the presence of an additional hydrogen-bonding site in the para-position of the boronic acids, the formation of 1D strands is induced, which generally supports interstrand pi-interactions to yield 2D layer structures. In most cases, adjacent bpe molecules in the crystal structures fulfill the topological criteria for a [2 + 2] photodimerization reaction and react to yield rctt-tetrakis(4-pyridyl)cyclobutane (tpcb). UV photoreaction experiments on single crystals for [(4-cpba)2(bpe)3] resulted in a single-crystal-to-single-crystal (SCSC) transformation. The boronic acid 4-cpba was also used to direct the photoreaction catalytically.
Details
- Title: Subtitle
- Crystal Engineering of Multiple Supramolecular Heterosynthons in Cocrystals of Boronic Acids: Structures, Photoreactivities, and Catalysis
- Creators
- Marcos Barba Hernandez - Univ Auto?noma Estado Morelos, Ctr Invest Qui?m, Inst Invest Ciencias Ba?sicas & Aplicadas, Cuernavaca 62209, Morelos, MexicoMaria Guadalupe Vasquez-Rios - Université de SherbrookeHerbert Hopfl - Universidad Autónoma del Estado de MorelosLeonard R. Macgillivray - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Crystal growth & design, Vol.25(1), pp.38-52
- Publisher
- Amer Chemical Soc
- DOI
- 10.1021/acs.cgd.4c01218
- ISSN
- 1528-7483
- eISSN
- 1528-7505
- Number of pages
- 15
- Grant note
- Canada Excellence Research Chair program Canada Excellence Research Chairs, Government of Canada Consejo Nacional de Ciencia y Tecnologia (CONACyT)
- Language
- English
- Date published
- 01/01/2025
- Academic Unit
- Chemistry
- Record Identifier
- 9984770888002771
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