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Reversible Single‐Crystal‐to‐Single‐Crystal Photochemical Formation and Thermal Cleavage of a Cyclobutane Ring
Author(s) -
Kole Goutam Kumar,
Kojima Tatsuhiro,
Kawano Masaki,
Vittal Jagadese J.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201306746
Subject(s) - cyclobutane , cleavage (geology) , photochemistry , chemistry , single crystal , ring (chemistry) , crystallography , cycloaddition , molecule , crystal (programming language) , kinetics , materials science , organic chemistry , catalysis , fracture (geology) , composite material , physics , quantum mechanics , computer science , programming language
A [2+2] cycloaddition reaction has been observed in a number of solids. The cyclobutane ring in a photodimerized material can be cleaved into olefins by UV light and heat. The high thermal stability of the metal–organic salt K 2 SDC (H 2 SDC=4,4’‐stilbenedicarboxylic acid) has been successfully utilized to investigate the reversible cleavage of a cyclobutane ring. The two polymorphs of K 2 SDC undergo reversible cyclobutane formation by UV light and cleavage by heat in cycles. Of these, one polymorph retains its single‐crystal nature during the reversible processes. Polymorphs are known to show different physical properties and chemical reactivities. This work reveals that the retention of single‐crystal nature is strongly associated with the packing of molecules, which is controlled by kinetics and thermodynamics. The photoemissive nature of the products makes this as a promising material for photoswitches and optical data storage devices.