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Department of Chemistry, Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
; Fax: +49 (0)6131-39 25396
School of Chemistry and Chemical Engineering, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Wushan, 510641 Guangzhou, China
; Fax: +86 20 87110245
Chem. Soc. Rev., 2013,42, 143-155
20 Jul 2012,
First published online
02 Oct 2012
The dimerization of anthracene by a [4π + 4π] cycloaddition is one of the oldest and best known reactions in photochemistry. In the series of tethered bichromophoric arenes, this reaction type could be extended to anthracene–naphthalene, naphthalene–naphthalene and recently even to anthracene–benzene and naphthalene–benzene systems. Cyclophanes, which can be regarded as twofold or multiple tethered systems, are not discussed here. The cycloisomerizations are performed by irradiation at the long-wavelength absorption (λ > 270 nm), whereas shorter wavelengths (λ < 270 nm) lead to cycloreversions, which can be also achieved by a thermal route. The systems represent therefore a P- and T-type photochromism, which can be used for optical or chiroptical switches. An acceleration of the switch is possible by a singlet energy transfer (light harvesting antenna effect) in dendritic compounds. In the past 5 to 10 years many applications of these switches were studied in the context of photonic devices, sensor techniques, lithographic processes, imaging techniques, data processing and data storage.
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