Towards thermally stable cyclophanediene-dihydropyrene photoswitches
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| 024 | 7 | 0 | |a 10.1007/s00894-015-2695-0 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2695-0 | ||
| 245 | 0 | 0 | |a Towards thermally stable cyclophanediene-dihydropyrene photoswitches |h [Elektronische Daten] |c [Nasir Khan, Nadeem Sheikh, Ather Khan, Ralf Ludwig, Tariq Mahmood, Wajid Rehman, Yasair Al-Faiyz, Khurshid Ayub] |
| 520 | 3 | |a 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. | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a DFT calculations |2 nationallicence | |
| 690 | 7 | |a Electrocyclization |2 nationallicence | |
| 690 | 7 | |a Photoswitches |2 nationallicence | |
| 690 | 7 | |a Rational design |2 nationallicence | |
| 690 | 7 | |a Sigmatropic rearrangement |2 nationallicence | |
| 690 | 7 | |a Thermal process |2 nationallicence | |
| 700 | 1 | |a Khan |D Nasir |u Department of Chemistry, COMSATS Institute of Information Technology, 22060, Abbottabad, Pakistan |4 aut | |
| 700 | 1 | |a Sheikh |D Nadeem |u Department of Chemistry, Faculty of Science, King Faisal University, P.O. Box 380, 31982, Al-Ahsa, Saudi Arabia |4 aut | |
| 700 | 1 | |a Khan |D Ather |u Interdisciplinary Research Center in Biomedical Materials, COMSATS Institute of Information Technology, Lahore, Pakistan |4 aut | |
| 700 | 1 | |a Ludwig |D Ralf |u Institut für Chemie, Physikalische und Theoretische Chemie, Universität Rostock, Dr.-Lorenz-Weg 1, 18059, Rostock, Germany |4 aut | |
| 700 | 1 | |a Mahmood |D Tariq |u Department of Chemistry, COMSATS Institute of Information Technology, 22060, Abbottabad, Pakistan |4 aut | |
| 700 | 1 | |a Rehman |D Wajid |u Department of Chemistry, Hazara University, Mansehra, Pakistan |4 aut | |
| 700 | 1 | |a Al-Faiyz |D Yasair |u Department of Chemistry, Faculty of Science, King Faisal University, P.O. Box 380, 31982, Al-Ahsa, Saudi Arabia |4 aut | |
| 700 | 1 | |a Ayub |D Khurshid |u Department of Chemistry, COMSATS Institute of Information Technology, 22060, Abbottabad, Pakistan |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/6(2015-06-01), 1-11 |x 1610-2940 |q 21:6<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2695-0 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00894-015-2695-0 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Khan |D Nasir |u Department of Chemistry, COMSATS Institute of Information Technology, 22060, Abbottabad, Pakistan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Sheikh |D Nadeem |u Department of Chemistry, Faculty of Science, King Faisal University, P.O. Box 380, 31982, Al-Ahsa, Saudi Arabia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Khan |D Ather |u Interdisciplinary Research Center in Biomedical Materials, COMSATS Institute of Information Technology, Lahore, Pakistan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Ludwig |D Ralf |u Institut für Chemie, Physikalische und Theoretische Chemie, Universität Rostock, Dr.-Lorenz-Weg 1, 18059, Rostock, Germany |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Mahmood |D Tariq |u Department of Chemistry, COMSATS Institute of Information Technology, 22060, Abbottabad, Pakistan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Rehman |D Wajid |u Department of Chemistry, Hazara University, Mansehra, Pakistan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Al-Faiyz |D Yasair |u Department of Chemistry, Faculty of Science, King Faisal University, P.O. Box 380, 31982, Al-Ahsa, Saudi Arabia |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Ayub |D Khurshid |u Department of Chemistry, COMSATS Institute of Information Technology, 22060, Abbottabad, Pakistan |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/6(2015-06-01), 1-11 |x 1610-2940 |q 21:6<1 |1 2015 |2 21 |o 894 | ||