Issue 9, 2011
From the journal:

Photochemical & Photobiological Sciences

Applications of hydrogen-bond-acceptor templates to direct ‘in-phase’ reactivity of a diene diacid in the solid state†‡

Manza B. J. Atkinson,§a   Anatoliy N. Sokolov,§a   Dejan-Krešimir Bučar,a   S. V. Santhana Mariappan,a   Martin T. Mwangi,a   Michael C. Tiedmana  and  Leonard R. MacGillivray*a  

* Corresponding authors

a Department of Chemistry, University of Iowa, Iowa City, Iowa, USA
E-mail: len-macgillivray@uiowa.edu
Fax: +1 319-335-1270
Tel: +1 319-335-3504

Abstract

The hydrogen-bond-acceptor (HBA) templates 2,3-bis(4-methylenethiopyridyl)naphthalene (2,3-nap) and 1,8-bis(4-pyridyl)naphthalene (1,8-dpn) are used to assemble (E,E)-2,5-dimethylmuconic acid (dmma) in the solid state for an intermolecular [2 + 2] photocycloaddition. Co-crystallisation of 2,3-nap with dmma affords an 1D hydrogen-bonded polymer that is photostable while 1,8-nap affords a 0D hydrogen-bonded assembly that is photoactive. The diene stacks in-phase and reacts to give a synmonocyclobutane in up to 55% yield.

Graphical abstract: Applications of hydrogen-bond-acceptor templates to direct ‘in-phase’ reactivity of a diene diacid in the solid state

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Article information

DOI
https://doi.org/10.1039/C1PP05077J
Article type
Communication
Submitted
19 Feb 2011
Accepted
22 Mar 2011
First published
09 Apr 2011

Photochem. Photobiol. Sci., 2011,10, 1384-1386

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Applications of hydrogen-bond-acceptor templates to direct ‘in-phase’ reactivity of a diene diacid in the solid state

M. B. J. Atkinson, A. N. Sokolov, D. Bučar, S. V. S. Mariappan, M. T. Mwangi, M. C. Tiedman and L. R. MacGillivray, Photochem. Photobiol. Sci., 2011, 10, 1384 DOI: 10.1039/C1PP05077J

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