Exploiting Boron Coordination: B←N Bond Supports a [2+2] Photodimerization in the Solid State and Generation of a Diboron Bis-Tweezer for Benzene/Thiophene Separation

Gonzalo Campillo-Alvarado; Kyle P D'mello; Dale C Swenson; S V Santhana Mariappan; Herbert Höpfl; Hugo Morales-Rojas; Leonard R MacGillivray

doi:10.1002/anie.201812174

Exploiting Boron Coordination: B←N Bond Supports a [2+2] Photodimerization in the Solid State and Generation of a Diboron Bis-Tweezer for Benzene/Thiophene Separation

Angew Chem Int Ed Engl. 2019 Apr 8;58(16):5413-5416. doi: 10.1002/anie.201812174. Epub 2019 Mar 12.

Authors

Gonzalo Campillo-Alvarado¹, Kyle P D'mello¹, Dale C Swenson¹, S V Santhana Mariappan¹, Herbert Höpfl², Hugo Morales-Rojas², Leonard R MacGillivray¹

Affiliations

¹ Department of Chemistry, University of Iowa, E555 Chemistry Building, Iowa City, IA, 52242, USA.
² Centro de Investigaciones Químicas, Instituto de Investigación en Ciencias Básicas y Aplicadas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, C.P., 62209, Cuernavaca, México.

PMID: 30770618
DOI: 10.1002/anie.201812174

Abstract

B←N coordination supports a [2+2] photodimerization in the solid state. The bond is defined by an orthogonal interaction between stilbazole and a phenylboronic ester to enable a stereocontrolled and rapid photoreaction. The cyclobutane photoproduct affords a novel diboron bis-tweezer adduct that is used to separate a mixture of benzene and thiophene upon crystallization.

Keywords: boron-nitrogen adducts; boronic ester; dimerization; molecular recognition; self-assembly.

Abstract

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