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Autori: Višnjevac, Aleksandar; Basarić, Nikola; Šindler-Kulyk, Marija; Kojić-Prodić, Biserka
Naslov: The crystal structure of 2,2'-(o-phenylenedivinylene)dibenzo[b]furan and its [3.2.1]bicyclic photoproduct
Izvornik: Tenth Croatian-Slovenian Crystallographic Meeting, Book of Abstracts / Popović, Stanko; Leban, Ivan (ur.). - Zagreb : Hrvatska kristalografska zajednica , 2001. 9.
Skup: Tenth Croatian-Slovenian Crystallographic Meeting
Mjesto i datum: Lovran, Hrvatska, 21-24.06.2001.
Sažetak:
Molecular and crystal structure of trans, trans-2,2'-(o-phenylenedivinylene) dibenzo[b]furane (1) and its [3.2.1] bicyclic photoproduct 13-exo-(2-benzo[b]furyl)-11,12-dihydro-6,11-methano-6H-benzo[4,5]cyclohepta[1,2-b]benzo[d]furan (2) are presented. It is well documented that heterocyclic derivatives of o-vinylstilbene upon exposure to UV radiation undergo different photochemical intra- and intermolecular transformations. Annelated furans react to give bicyclo[3.2.1]octadiene derivatives (intramolecular photoreaction) and cyclobutan dimers as products of an intermolecular photocycloaddition. In solutions of higher concentrations, however, only products of an intermolecular photoreaction were isolated. Furthermore, it is known that bb'-dikinoxalyn derivatives of o-divinylbenzene do not undergo photochemical transformation in solid state at all, due to too long intermolecular distances inside the crystal. Our aim is to investigate the photochemistry of 1 in solutions of higher and lower concentrations, as well as in solid state. Having in mind photochemical behaviour of the related compounds in solid state, it was of particular interest to establish the details of the crystal structure of 1 (Fig.1), and to identify its photoproduct 2 (Fig.2) unambigously, by X-ray diffraction methods. 1 crystallizes in orthorhombic Pccn space group with Z = 4. The molecule of 1 reveals C2 symmetry. a = 5.8726(9) Ĺ, b = 20.849(2) Ĺ, c = 15.563(5) Ĺ, V = 1905.6 (7) Ĺ3, Dx = 1.266(2) gcm-3, R1 = 0.0468, wR2 = 0.1310, 1942 reflexions. The crystal packing is guided by weak intermolecular p- p interactions (Fig.3). 2 crystallizes in monoclinic P21/c space group with Z = 4. a = 8.515(3) Ĺ, b = 11.839(4) Ĺ, c = 17.799(6) Ĺ, V = 1791 (1) Ĺ3, Dx = 1.344(2) gcm-3, R1 = 0.0681, wR2 = 0.1958, 3628 reflexions.
Vrsta sudjelovanja: Predavanje
Vrsta prezentacije u zborniku: Sažetak
Vrsta recenzije: Međunarodna recenzija
Projekt / tema: 00980608, 125004
Izvorni jezik: ENG
Kategorija: Znanstveni
Znanstvena područja:
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