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Regioselective photoreactions within a series of mixed co-crystals containing isosteric dihalogenated resorcinols with 4-stilbazole

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Abstract

The formation and photoreactivity of a series of mixed co-crystals containing 4-stilbazole along with both 4,6-dichlororesorcinol and 4,6-dibromoresorcinol at various ratios is reported. In all cases, the quantitative [2 + 2] cycloaddition reaction yields an identical head-to- tail photoproduct, namely rctt-1,3-bis(4-pyridyl)-2,4-bis (phenyl)cyclobutane. The selectivity in the cycloaddition reaction occurred due to a shorter distance observed between two carbon–carbon double bonds that were found between and not within the hydrogen-bonded assemblies.

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Authors and Affiliations

  1. Department of Biological Sciences, Webster University, 470 East Lockwood Ave., St. Louis, MO, 63119, USA

    Anna L. Grobelny & Ryan H. Groeneman

  2. Department of Chemistry and Biochemistry and the Center for Nanoscience, University of Missouri-St. Louis, 1 University Blvd., St. Louis, MO, 63121, USA

    Nigam P. Rath

Authors
  1. Anna L. Grobelny
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  2. Nigam P. Rath
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  3. Ryan H. Groeneman
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Corresponding author

Correspondence to Ryan H. Groeneman.

Additional information

Electronic supplementary information (ESI) available: Experimental details, single crystal and powder X-ray data, and 1H NMR spectra. CCDC 1867907–1867910. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9pp00004f

The initial percent of (4,6-diCl res) and (4,6-diBr res) within each mixed cocrystal was based upon the stoichiometric amounts used in the co-crystallization process.

The experimental percent of (4,6-diCl res) and (4,6-diBr res) within each mixed co-crystal was determined from diffraction data by using free variable refinements to obtain the relative ratio of each component.

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Grobelny, A.L., Rath, N.P. & Groeneman, R.H. Regioselective photoreactions within a series of mixed co-crystals containing isosteric dihalogenated resorcinols with 4-stilbazole. Photochem Photobiol Sci 18, 989–992 (2019). https://doi.org/10.1039/c9pp00004f

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  • DOI: https://doi.org/10.1039/c9pp00004f

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