Theoretical Study of Photochromic Compounds, Part 2: Thermal Mechanism for Byproduct Formation and Fatigue Resistance of Diarylethenes Used as Data Storage Materials

    Authors

    P. D. Patel; I. A. Mikhailov; K. D. Belfield;A. E. Masunov

    Comments

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    Abbreviated Journal Title

    Int. J. Quantum Chem.

    Keywords

    electrocyclic reaction; chemical kinetics; byproduct formation; fatigue; resistance; SINGLE-CRYSTALLINE PHOTOCHROMISM; CYCLOHEXADIENE/HEXATRIENE; PHOTOCHEMICAL INTERCONVERSION; MOLECULAR SWITCHING DEVICE; AB-INITIO; ELECTROCYCLIC REACTION; REACTION DYNAMICS; REVERSIBLE PHOTOCYCLIZATION; DITHIENYLETHENE DERIVATIVES; CONICAL INTERSECTIONS; TRANSITION-STATES; Chemistry, Physical; Mathematics, Interdisciplinary Applications; Physics, Atomic, Molecular & Chemical

    Abstract

    Certain organic compounds possess the ability to change color under the influence of light, called photochromism. This change is due to ultrafast chemical transition from open to closed ring isomers (photocyclization), which can be used for optical data storage and photoswitching applications. These applications require minimization of the irreversible photodegradation of the material, called photofatigue. This property is related to the chemical rate of byproduct formation. We use density functional theory methods to predict the mechanism and activation barriers to the byproduct formation for 1,2-bis(2-methyl-5-phenyl-3-thienyl)perfluorocyclopentene in order to estimate its fatigue resistance. We also explain higher fatigue resistance for its methylated derivative. The methods used in this study may become a part of rational design strategy for the new photochromic materials. (C) 2009 Wiley Periodicals, Inc. Int J Quantum Chem 109: 3711-3722, 2009

    Journal Title

    International Journal of Quantum Chemistry

    Volume

    109

    Issue/Number

    15

    Publication Date

    1-1-2009

    Document Type

    Article; Proceedings Paper

    Language

    English

    First Page

    3711

    Last Page

    3722

    WOS Identifier

    WOS:000271404600024

    ISSN

    0020-7608

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