Towards thermally stable cyclophanediene-dihydropyrene photoswitches
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- 作者：Nasir Khan ; Nadeem S. Sheikh ; Ather F. Khan ; Ralf Ludwig…
- 关键词：DFT calculations ; Electrocyclization ; Photoswitches ; Rational design ; Sigmatropic rearrangement ; Thermal process
- 刊名：Journal of Molecular Modeling
- 出版年：2015
- 出版时间：June 2015
- 年：2015
- 卷：21
- 期：6
- 全文大小：1,640 KB
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Nadeem S. Sheikh (3)
Ather F. Khan (4)
Ralf Ludwig (5) (6)
Tariq Mahmood (1)
Wajid Rehman (2)
Yasair S. S. Al-Faiyz (3)
Khurshid Ayub (1) (3)
1. Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, Pakistan, 22060
2. Department of Chemistry, Hazara University, Mansehra, Pakistan
3. Department of Chemistry, Faculty of Science, King Faisal University, P.O. Box 380, Al-Ahsa, 31982, Saudi Arabia
4. Interdisciplinary Research Center in Biomedical Materials, COMSATS Institute of Information Technology, Lahore, Pakistan
5. Institut f眉r Chemie, Physikalische und Theoretische Chemie, Universit盲t Rostock, Dr.-Lorenz-Weg 1, 18059, Rostock, Germany
6. Leibniz-Institut f眉r Katalyse an der Universit盲t Rostock e. V, Alebert-Einstein-Strasse 29a, 18059, Rostock, Germany - 刊物类别：Chemistry and Materials Science
- 刊物主题：Chemistry
Computer Applications in Chemistry
Biomedicine
Molecular Medicine
Health Informatics and Administration
Life Sciences
Computer Application in Life Sciences - 出版者：Springer Berlin / Heidelberg
- ISSN：0948-5023
文摘
Cyclophanediene dihydropyrenes (CPD-DHP) are photochromic compounds because they change their color by irradiation with lights of different color. Potential use of CPD-DHP photoswitch in memory devices requires a very slow thermal return in the dark in the absence of any side reaction. Herein, thermal return of CPDs to DHPs, and an unwanted sigmatropic shift in DHP is studied through density functional theory calculations at (U)B3LYP/6-31+G(d). The thermal return occurs through symmetry forbidden conrotatory electrocyclic reaction. Dimethyl amino CPD-DHP photoswitch pair has the highest activation barrier for electrocyclization and sigmatropic shifts. The lowest activation barrier for symmetry forbidden electrocyclization is observed for GeBr3 functionalized CPD. An unprecedented decomposition pathway involving elimination of the internal substituents is predicted for Cl, Br and SMe functionalized DHPs. This study shows great promise in understanding the Woodward Hoffmann forbidden processes and, in reducing the synthetic efforts toward robust photochromes for memory applications.