Packing-dependent photochromism: The case of photoinduced intramolecular proton transfer in 6-(2′,4′-dinitrobenzyl)-2,2′-bipyridine

Pance Naumov, Yuji Ohashi

Research output: Contribution to journalArticle

Abstract

A new photoactive monoclinic polymorph (γ-form) of 6-(2′,4′-dinitrobenzyl)-2,2′-bipyridine was obtained from an acetone-methanol solution. The crystal structure was compared with those of two polymorphs reported previously (photoactive orthorhombic α-form and photoinactive monoclinic β-form) and with structures of related nitrobenzylpyridines to explain the relation between the structure and photochromism. The comparison of the reaction cavities around the reactive pyridyl-benzyl-nitro fragment among the polymorphs and related nitrobenzylpyridines revealed that a crucial factor for photochromic activity is the rotational freedom of the ortho-nitro group in their crystals and its accessibility from the proton-donor and proton-acceptor sites. This is because the ortho-nitro group should rotate around the N-C bond to transfer a proton from the methylene group to the N atom of the pyridine ring.

Original languageEnglish (US)
Pages (from-to)343-349
Number of pages7
JournalActa Crystallographica Section B: Structural Science
Volume60
Issue number3
DOIs
StatePublished - Jun 1 2004

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

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