Rapid decoloration and acidichromism of photochromic 3,3-diaryl-3H-pyrano[3,2-f]quinolines |
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| Affiliation: | 1. Key Laboratory of Systems Bioengineering (Ministry of Education), School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, PR China;2. College of Chemistry, Nankai University, Tianjin 300071, PR China;1. Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt;2. Medicinal Chemistry Department, Faculty of Pharmacy, Port-Said University, Port-Said 42526, Egypt;3. Department of Medicinal Chemistry, Faculty of Pharmacy, Minia University, 61519 El Minia, Egypt;4. Institute of Toxikology and Genetics, Karlsruhe Institute of Technology, Hermann-von-Helmholtz Platz 1, Campus Nord, 76344 Eggenstein-Leopoldshafen, Germany;5. Institute of Toxikologie und Genetik, Hermann-von-Helmholtz Platz 1, Campus Nord, 76344 Eggenstein-Leopoldshafen, Germany;6. Department of Chemistry, University of Helsinki, PO Box 55 (A. I. Virtasen aukio I), 00014 University of Helsinki, Finland;7. Centre for Biomedicine and Medical Technology Mannheim, Medical Faculty Mannheim, University of Heidelberg, 68167 Mannheim, Germany;8. Division of Chemical Biology and Medicinal Chemistry, The University of Texas at Austin, Austin, TX 78712, USA;1. State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy and Tianjin Key Laboratory of Molecular Drug Research, Nankai University, Tianjin, People''s Republic of China;2. CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, People''s Republic of China;1. Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, China;2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China;1. Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University, Changsha 410081, China;2. Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081, China;3. Beijing National Laboratory for Molecular Sciences (BNLMS), Peking University, Beijing 100871, PR China;1. Institute of Chemistry, University of the Punjab, Lahore, Pakistan;2. Department of Chemistry, Government College University, Lahore, Pakistan;3. Department of Applied Chemistry, Government College University, Faisalabad, Pakistan;4. Department of Chemistry, Faculty of Science, King Abdul aziz University, Jeddah, Saudi Arabia;5. Department of Chemistry Islamia, University of Bahawalpur, Bahawalpur, Pakistan;6. Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah 21589, P. O. Box 80203, Saudi Arabia |
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| Abstract: | Pyranoquinoline, with its light-sensitive fragment and coordination node, provides an ideal matrix for the development of multi-functional photochromic compounds. This paper presents the synthesis and photochromic properties of 3,3-diaryl-3H-pyrano[3,2-f]quinoline derivatives QP1-QP8. All exhibited good photochromism under UV light irradiation followed by biexponential kinetic decay in the dark at ambient temperature. Their photochromic processes were reversible, and acidichromism was observed to occur in solution. The fading speeds of QP2 and QP6 were higher than those of their known naphthopyran counterparts, whereas the decoloring speeds of the six other compounds were all over an order of magnitude higher than those of QP2 and QP6. The synthesized pyranoquinolines exhibited very good fatigue resistance both in solution and the solid state. Compared to other pyranoquinolines, the optical densities of QP2 and QP6, i.e., the compounds with 2,4-dimethoxylphenyl and 1-naphthyl, were enhanced dramatically. For all the synthesized pyranoquinolines, a distinct bathochromic shift was observed with increasing solvent polarity. The structure-property relationship of the pyranoquinolines was revealed through the single-crystal X-ray analysis of QP1 and QP7. |
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| Keywords: | Pyranoquinolines Photochromism Acidichromism Fading speed Bathochromic shift |
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