Journal article
Application of Long-Range Synthon Aufbau Modules Based on Trihalophenols To Direct Reactivity in Binary Cocrystals: Orthogonal Hydrogen Bonding and π–π Contact Driven Self-Assembly with Single-Crystal Reactivity
Crystal growth & design, Vol.19(5), pp.2511-2518
05/01/2019
DOI: 10.1021/acs.cgd.9b00035
Abstract
The ability of 2,4,6-trihalophenols (3X-phOH) (where X = F, Cl, or Br) to enable reactivity of 1,2-bis(4-pyridyl)ethylene (bpe) in the solid state via cocrystallization is reported. The trihalophenols display structure behavior defined by infinite face-to-face π···π contacts and hydrogen bonds as pure solids that we show can be transferred to binary cocrystals to organize bpe to undergo a solid-state photodimerization. Cocrystals based on Cl- and Br-halophenols undergo single-crystal-to-single-crystal photoreactions to afford rctt-tetrakis(4-pyridyl)cyclobutane (tpcb) stereoselectively and in near quantitative yield. The use of 3X-phOH to enable reactivity in the solid state is discussed in the context of long-range synthon Aufbau modules.
Details
- Title: Subtitle
- Application of Long-Range Synthon Aufbau Modules Based on Trihalophenols To Direct Reactivity in Binary Cocrystals: Orthogonal Hydrogen Bonding and π–π Contact Driven Self-Assembly with Single-Crystal Reactivity
- Creators
- Gonzalo Campillo-Alvarado - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesChangan Li - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United StatesDale C Swenson - 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.19(5), pp.2511-2518
- DOI
- 10.1021/acs.cgd.9b00035
- ISSN
- 1528-7483
- eISSN
- 1528-7505
- Grant note
- DOI: 10.13039/100000078, name: Division of Materials Research, award: DMR-1708673; DOI: 10.13039/501100003141, name: Consejo Nacional de Ciencia y Tecnolog?a
- Language
- English
- Date published
- 05/01/2019
- Academic Unit
- Chemistry; Pharmaceutical Sciences and Experimental Therapeutics
- Record Identifier
- 9984216717602771
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