Issue 6, 2002
From the journal:

Photochemical & Photobiological Sciences

Fluorine in crystal engineering: photodimerization of (1E,3E)-1-phenyl-4-pentafluorophenylbuta-1,3-dienes in the crystalline state

Kodumuru Vishnumurthy,†*a   Tayur N. Guru Row*a  and  Kailasam Venkatesana  

* Corresponding authors

a Department of Organic Chemistry, Indian Institute of Science, Bangalore, India
E-mail: kvishnumurthy@hotmail.com

Abstract

(1E,3E)-1,4-Diphenylbuta-1,3-diene is photostable in the crystalline state, while fluoro-substitution induces reactivity. Crystals of (1E,3E)-1-pentafluorophenyl-4-(4-methoxyphenyl)buta-1,3-diene 1, (1E,3E)-1-pentafluorophenyl-4-(4-methylphenyl)buta-1,3-diene 2 and (1E,3E)-1-pentafluorophenyl-4-phenylbuta-1,3-diene 3 undergo double [2+2] photodimerization topochemically to yield anti head-to-tail photodimers in the crystalline state. Remarkably fluoro-substitution brings the reactant molecules into an anti head-to-tail arrangement in the crystal lattice with weak intermolecular interactions: C–H⋯F, F⋯F, C–H⋯π, π⋯π.

Graphical abstract: Fluorine in crystal engineering: photodimerization of (1E,3E)-1-phenyl-4-pentafluorophenylbuta-1,3-dienes in the crystalline state

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Article information

DOI
https://doi.org/10.1039/B202557D
Article type
Paper
Submitted
13 Mar 2002
Accepted
01 May 2002
First published
17 May 2002

Photochem. Photobiol. Sci., 2002,1, 427-430

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Fluorine in crystal engineering: photodimerization of (1E,3E)-1-phenyl-4-pentafluorophenylbuta-1,3-dienes in the crystalline state

K. Vishnumurthy, T. N. Guru Row and K. Venkatesan, Photochem. Photobiol. Sci., 2002, 1, 427 DOI: 10.1039/B202557D

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