Computational and Crystallographic Examination of Naphthoquinone Based Diarylethene Photochromes
| Autor: | William R. Quigley, Martial Boggio-Pasqua, Dinesh G. Patel, Ian M. Walton, Travis Mitchell, Frank A. Novak |
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| Přispěvatelé: | Department of Chemistry, The Pennsylvania State University, Pennsylvania State University (Penn State), Penn State System-Penn State System, Photochimie théorique et computationnelle (LCPQ) (PTC), Laboratoire de Chimie et Physique Quantiques (LCPQ), Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes (IRSAMC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Department of Chemistry, the State University of New York at Buffalo, Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse) |
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Materials science
Light Absorption spectroscopy Ultraviolet Rays Molecular Conformation Pharmaceutical Science Crystallography X-Ray 010402 general chemistry Ring (chemistry) 01 natural sciences Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Photochromism Computational Chemistry Diarylethene lcsh:Organic chemistry Drug Discovery Thermal stability Physical and Theoretical Chemistry TD-DFT computations quinones Molecular Structure 010405 organic chemistry Aryl TD–DFT computations Organic Chemistry Ethylenes Photochemical Processes 3. Good health 0104 chemical sciences Quinone diarylethenes [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry Crystallography chemistry Chemistry (miscellaneous) Molecular Medicine Density functional theory photochromes Naphthoquinones |
| Zdroj: | Molecules Molecules, MDPI, 2020, 25 (11), pp.2630. ⟨10.3390/molecules25112630⟩ Volume 25 Issue 11 Molecules, Vol 25, Iss 2630, p 2630 (2020) |
| ISSN: | 1420-3049 |
| Popis: | Photochromic compounds have a lengthy history of study and a profusion of applications that stand to gain from these studies. Among the classes of photochromic compounds, diarylethenes show desirable properties including high fatigue resistance and thermal stability, thus meeting some of the most important criteria necessary to enter the realm of practical applications. Recently, photochromic diarylethenes containing quinone functionalities have demonstrated interesting optical and solid-state properties. When properly interfaced with suitable electron withdrawing groups on the aryl component, both the ring-opening and ring-closing reactions can be achieved with visible light this is in contrast to most other diarylethenes where UV light is required for ring closure. Unfortunately, quantitative conversion from open to closed forms is not possible. In this work, we examine the relative energies of conformations of solid-state structures observed by X-ray crystallography and evaluate their thermal stabilities based on density functional theory (DFT) calculations. Time-dependent DFT (TD&ndash DFT) is used to model the UV-vis absorption spectra of these quinone diarylethenes. We show that spectral overlap between open and closed forms is a major hindrance to full photoconversion. |
| Databáze: | OpenAIRE |
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