Journal article
Hydrogen- and Halogen-Bonded Binary Cocrystals with Ditopic Components: Systematic Structural and Photoreactivity Properties That Provide Access to a Completed Series of Symmetrical Cyclobutanes
Crystal growth & design, Vol.20(11), pp.7501-7515
11/04/2020
DOI: 10.1021/acs.cgd.0c01143
Abstract
A series of binary cocrystals involving the ditopic hydrogen- and halogen-bond (H- and X-bond, respectively) donors resorcinol (res) and hydroquinone (hq), and 1,3- and 1,4-diiodotetrafluorobenzene (1,3- and 1,4-di-I-tFb), respectively, cocrystallized with one of the three symmetric bipyridines trans-1,2-bis(n-pyridyl)ethylene (n,n′-bpe, where n = n′ = 2, 3, 4) is reported. The structures of the six novel cocrystals, (1,3-di-I-tFb)·(3,3′-bpe), 4(res)·3(3,3′-bpe), (1,3-di-I-tFb)·(4,4′-bpe), 3(hq)·2(2,2′-bpe), (1,4-di-I-tFb)·(3,3′-bpe), and (hq)·(3,3′-bpe), are described. The cocrystals comprise components that assemble by either O-H···N and O-H···O H-bonds (res and hq) or N···I X-bonds (1,3- and 1,4-di-I-tFb). The work completes a series of 18 cocrystals involving either the three dihydroxybenzenes catechol (cat), res, and hq or the three diiodotetrafluorobenzenes (1,2-, 1,3-, and 1,4-di-I-tFb) as H- or X-bond donors, respectively, with each of the three structurally isomeric symmetric bipyridines n,n′-bpe. Our study demonstrates the significant consequences that minimally subtle variations to molecular structure of coformers can have for stoichiometric formulations, molecular packing, and solid-state photoreactivity. The work also provides access to a completed series of symmetrically substituted rctt-tetrakis(n-pyridyl)cyclobutanes (where: n = 2, 3, or 4).
Details
- Title: Subtitle
- Hydrogen- and Halogen-Bonded Binary Cocrystals with Ditopic Components: Systematic Structural and Photoreactivity Properties That Provide Access to a Completed Series of Symmetrical Cyclobutanes
- Creators
- Jay Quentin - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesLeonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
- Resource Type
- Journal article
- Publication Details
- Crystal growth & design, Vol.20(11), pp.7501-7515
- DOI
- 10.1021/acs.cgd.0c01143
- ISSN
- 1528-7483
- eISSN
- 1528-7505
- Grant note
- DOI: 10.13039/100000001, name: National Science Foundation, award: DMR-1708673
- Language
- English
- Date published
- 11/04/2020
- Academic Unit
- Chemistry; Pharmaceutical Sciences and Experimental Therapeutics
- Record Identifier
- 9984216574302771
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