Journal article
Structures and Reactivities of Cocrystals Involving Diboronic Acids and Bipyridines: In Situ Linker Reaction and 1D-to-2D Dimensionality Change via Crystal-to-Crystal Photodimerization
Chemistry : a European journal, Vol.28(25), pp.e202104604-n/a
05/02/2022
DOI: 10.1002/chem.202104604
PMCID: PMC9310599
PMID: 35274391
Appears in UI Libraries Support Open Access
Abstract
Cocrystallizations of diboronic acids [1,3-benzenediboronic acid (1,3-bdba), 1,4-benzenediboronic acid (1,4-bdba) and 4,4'-biphenyldiboronic acid (4,4'-bphdba)] and bipyridines [1,2-bis(4-pyridyl)ethylene (bpe) and 1,2-bis(4-pyridyl)ethane (bpeta)] generated the hydrogen-bonded 1 : 2 cocrystals [(1,4-bdba)(bpe)(2)] (1), [(1,4-bdba)(bpeta)(2)] (2), [(1,3-bdba)(bpe)(2)(H2O)(2)] (3) and [(1,3-bdba)(bpeta)(2)(H2O)] (4), wherein 1,3-bdba involved hydrated assemblies. The linear extended 4,4'-bphdba exhibited the formation of 1 : 1 cocrystals [(4,4'-bphdba)(bpe)] (5) and [(4,4'-bphdba-me)(bpeta)] (6). For 6, a hemiester was generated by an in-situ linker transformation. Single-crystal X-ray diffraction revealed all structures to be sustained by B(O)-H center dot center dot center dot N, B(O)-H center dot center dot center dot O, O-w-H center dot center dot center dot O, O-w-H center dot center dot center dot N, C-H center dot center dot center dot O, C-H center dot center dot center dot N, pi center dot center dot center dot pi, and C-H center dot center dot center dot pi interactions. The cocrystals comprise 1D, 2D, and 3D hydrogen-bonded frameworks with components that display reactivities upon cocrystal formation and within the solids. In 1 and 3, the C=C bonds of the bpe molecules undergo a [2+2] photodimerization. UV radiation of each compound resulted in quantitative conversion of bpe into cyclobutane tpcb. The reactivity involving 1 occurred via 1D-to-2D single-crystal-to-single-crystal (SCSC) transformation. Our work supports the feasibility of the diboronic acids as formidable structural and reactivity building blocks for cocrystal construction.
Details
- Title: Subtitle
- Structures and Reactivities of Cocrystals Involving Diboronic Acids and Bipyridines: In Situ Linker Reaction and 1D-to-2D Dimensionality Change via Crystal-to-Crystal Photodimerization
- Creators
- Maria Guadalupe Vasquez-Rios - University of IowaGonzalo Campillo-Alvarado - University of Illinois Urbana-ChampaignDale C. Swenson - University of IowaHerbert Hopfl - Universidad Autónoma del Estado de MorelosLeonard R. MacGillivray - University of Iowa
- Resource Type
- Journal article
- Publication Details
- Chemistry : a European journal, Vol.28(25), pp.e202104604-n/a
- DOI
- 10.1002/chem.202104604
- PMID
- 35274391
- PMCID
- PMC9310599
- NLM abbreviation
- Chemistry
- ISSN
- 0947-6539
- eISSN
- 1521-3765
- Publisher
- Wiley
- Number of pages
- 11
- Grant note
- NSF DMR-1708673; CHE-1828117 / National Science Foundation; National Science Foundation (NSF) Office for Access and Equity CONACyT; Consejo Nacional de Ciencia y Tecnologia (CONACyT) Illinois Materials Research Science and Engineering Center (University of Illinois at Urbana-Champaign) DRIVE Committee through the DRIVE Distinguished Postdoctoral Fellowship
- Language
- English
- Date published
- 05/02/2022
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984323339202771
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