caa a22 4500 475760476 CHVBK 20180406123549.0 cr unu---uuuuu 170329e20001001xx s 000 0 eng 10.1007/BF02496349 doi (NATIONALLICENCE)springer-10.1007/BF02496349 Photochromic dihetarylethenes [Elektronische Daten] 5. Synthesis, structure, and photochromic properties of 4,4′-disubstituted 1,2-bis [2-ethyl-5-ethylthio(ethylsulfonyl)-3-thienyl]perfluorocyclopentenes [M. Krayushkin, M. Kalik, D. Dzhavadov, L. Vorontsova, Z. Starikova, A. Martynkin, V. Ivanov, B. Uzhinov] A series of new photochromic compounds were obtained for the first time from 1,2-bis(2-ethylthio-3-thienyl)perfluorocyclopentene by substituting bromine atoms or carboxy, alkoxycarbonyl, and carbamoyl groups for hydrogen atoms in positions 4 and 4′. Introduction of these substituents causes a slight bathochromic shift (by 20-30 nm) of a long-wavelength absorption band for the cyclic form and significantly increases the quantum yields of photocyclization ФA→B and ring opening ФB→A. Depending on the nature of a substituent, ФA→B decreases in the order COOH>COOMe>CONHAr. The quantum yields are markedly reduced when the ethylthio groups in positions 5 and 5′ are replaced by ethylsulfonyl groups (a tenfold reduction in ФA→B and a four- to fivefold reduction in ФB→A) The most considerable bathochromic shift of a long-wavelength band and the highest quantum yields of forward and reverse photoreactions were observed for 1,2-bis(4-bromo-2-ethylthio-3-thienyl) perfluorocyclopentene. 1,2- Bis (2-ethyl-5-ethylthio-4-methoxycarbonyl-3-thienyl)perfluorocyclopentene was structurally characterized by X-ray diffraction analysis. Kluwer Academic/Plenum Publishers, 2000 bisthienylperfluorocyclopenentens nationallicence molecular structure nationallicence photochromic compounds nationallicence reversible photocyclization nationallicence quantum yield nationallicence Krayushkin M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut Kalik M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut Dzhavadov D. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut Vorontsova L. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut Starikova Z. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut Martynkin A. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut Ivanov V. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut Uzhinov B. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/10(2000-10-01), 1757-1762 1066-5285 49:10<1757 2000 49 11172 https://doi.org/10.1007/BF02496349 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02496349 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Krayushkin M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Kalik M. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Dzhavadov D. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Vorontsova L. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Starikova Z. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Martynkin A. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp, 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Ivanov V. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Uzhinov B. Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/10(2000-10-01), 1757-1762 1066-5285 49:10<1757 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer