Journal article
Halogen-Bond Mediated [2+2] Photodimerizations: À la Carte Access to Unsymmetrical Cyclobutanes in the Solid State
Molecules (Basel, Switzerland), Vol.27(3), p.1048
02/03/2022
DOI: 10.3390/molecules27031048
PMCID: PMC8839528
PMID: 35164313
Abstract
The ditopic halogen-bond (X-bond) donors 1,2-, 1,3-, and 1,4-diiodotetrafluorobenzene (
,
, and
, respectively) form binary cocrystals with the unsymmetrical ditopic X-bond acceptor
-1-(2-pyridyl)-2-(4-pyridyl)ethylene (
). The components of each cocrystal (
)·(
), (
)·(
), and (
)·(
) assemble via N···I X-bonds. For (
)·(
) and (
)·(
), the X-bond donor supports the C=C bonds of
to undergo a topochemical [2+2] photodimerization in the solid state: UV-irradiation of each solid resulted in stereospecific, regiospecific, and quantitative photodimerization of
to the corresponding head-to-tail (
) or head-to-head (
) cyclobutane photoproduct, respectively.
Details
- Title: Subtitle
- Halogen-Bond Mediated [2+2] Photodimerizations: À la Carte Access to Unsymmetrical Cyclobutanes in the Solid State
- Creators
- Jay Quentin - Department of Chemistry, University of Iowa, Iowa City, IA 52242, USAEric W Reinheimer - Rigaku Americas Corporation, 9009 New Trails Drive, The Woodlands, TX 77381, USALeonard R MacGillivray - Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA
- Resource Type
- Journal article
- Publication Details
- Molecules (Basel, Switzerland), Vol.27(3), p.1048
- DOI
- 10.3390/molecules27031048
- PMID
- 35164313
- PMCID
- PMC8839528
- NLM abbreviation
- Molecules
- eISSN
- 1420-3049
- Grant note
- DMR-1708673, CHE-1828117 / National Science Foundation
- Language
- English
- Date published
- 02/03/2022
- Academic Unit
- Pharmaceutical Sciences and Experimental Therapeutics; Chemistry
- Record Identifier
- 9984216691502771
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