Jump to main content
Jump to site search

Issue 9, 2011
Previous Article Next Article

Solid state double [2 + 2] photochemical reactions in the co-crystal forms of 1,5-bis(4-pyridyl)-1,4-pentadiene-3-one: establishing mechanism using single crystal X-ray, UV and 1H NMR

Author affiliations

Abstract

Double [2 + 2] photochemical reaction of 1,5-bis(4-pyridyl)-1,4-pentadiene-3-one (1P) was observed with 100% yield in four co-crystal forms of 1P with the hydrogen bonding template molecule phloroglucinol (PG) or 5-methoxy resorcinol (MR). The crystal structure of compound 1P does not have the required geometry to produce the double [2 + 2] reaction product, but it gives a single [2 + 2] reaction product with 15% yield upon time restricted irradiation. All the reactions in co-crystals of 1P resulted in the stereospecific exoexotetrapyridyl tricyclo[6.2.0.03,6]-decane. 1H NMR and the UV-vis spectroscopic studies clearly established a stepwise mechanism for this reaction through the formation of monocyclobutane intermediate. One co-crystal form of 1P with PG and another co-crystal form of 1P with resorcinol were found to be unreactive due to different reasons. Furthermore the mechanochemical grinding products of 1P with RN or MR have exhibited similar structural and reactivity correlations with those crystallized from solution.

Graphical abstract: Solid state double [2 + 2] photochemical reactions in the co-crystal forms of 1,5-bis(4-pyridyl)-1,4-pentadiene-3-one: establishing mechanism using single crystal X-ray, UV and 1H NMR

Back to tab navigation

Supplementary files

Article information


Submitted
07 Sep 2010
Accepted
26 Jan 2011
First published
16 Feb 2011

CrystEngComm, 2011,13, 3246-3257
Article type
Paper

Solid state double [2 + 2] photochemical reactions in the co-crystal forms of 1,5-bis(4-pyridyl)-1,4-pentadiene-3-one: establishing mechanism using single crystal X-ray, UV and 1H NMR

R. Santra and K. Biradha, CrystEngComm, 2011, 13, 3246
DOI: 10.1039/C0CE00612B

Social activity

Search articles by author

Spotlight

Advertisements