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Synthesis, Photophysical, and Electrochemical Properties of Pyrenes Substituted with Donors or Acceptors at the 4- or 4,9-Positions

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العنوان: Synthesis, Photophysical, and Electrochemical Properties of Pyrenes Substituted with Donors or Acceptors at the 4- or 4,9-Positions
المؤلفون: Holger Braunschweig, Katharina Edkins, Lei Ji, Todd B. Marder, Martin Haehnel, Ivo Krummenacher, Alexandra Friedrich, Andreas Lorbach
المصدر: Ji, L, Krummenacher, I, Friedrich, A, Lorbach, A, Haehnel, M, Edkins, K, Braunschweig, H & Marder, T B 2018, ' Synthesis, Photophysical, and Electrochemical Properties of Pyrenes Substituted with Donors or Acceptors at the 4-or 4,9-Positions ', Journal of Organic Chemistry, vol. 83, no. 7, pp. 3599-3606 . https://doi.org/10.1021/acs.joc.7b03227
بيانات النشر: American Chemical Society (ACS), 2018.
سنة النشر: 2018
مصطلحات موضوعية: 010405 organic chemistry, Chemistry, Pinacol, Organic Chemistry, 010402 general chemistry, Electrochemistry, 01 natural sciences, Acceptor, Borylation, Fluorescence, 0104 chemical sciences, chemistry.chemical_compound, Polymer chemistry, Surface modification, Pyrene
الوصف: We report herein an efficient and direct functionalization of the 4,9-positions of pyrene by Ir-catalyzed borylation. Three pinacol boronates (-Bpin), including 4-(Bpin)-2,7-di-(tert-butyl)pyrene (5), 4,9-bis(Bpin)-2,7-di-(tert-butyl)pyrene (6), and 4,10-bis(Bpin)-2,7-di-(tert-butyl)pyrene (7) were synthesized. The structures of 6 and 7 have been confirmed by single-crystal X-ray diffraction. To demonstrate the utility of these compounds, donor (NPh2) substituted compounds 4-diphenylamino-2,7-di-(tert-butyl)pyrene (1) and 4,9-bis(diphenylamino)-2,7-di-(tert-butyl)pyrene (2) have been synthesized on a gram scale. Acceptor (BMes2) substituted compounds 4,9-bis(BMes2)pyrene (3) and 4,9-bis(BMes2)-1,2,3,6,7,8-hexahydropyrene (4) were synthesized for comparison. The photophysical and electrochemical properties of compounds 1-4 have been studied both experimentally and theoretically. The S0S1 transitions of the 4,9-disubstituted pyrenes, 1-3, are allowed, with moderate fluorescence quantum yields and radiative decay rates. The photophysical and electrochemical properties of 1-3 were compared with the 2,6-naphthalenylene-cored compound 4 as well as the previously reported 2,7- and 1,6- pyrenylene-cored compounds.
وصف الملف: application/pdf
تدمد: 1520-6904
0022-3263
URL الوصول: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::42355faaabf1e299ca573eb14091429b
https://doi.org/10.1021/acs.joc.7b03227
حقوق: OPEN
رقم الأكسشن: edsair.doi.dedup.....42355faaabf1e299ca573eb14091429b
قاعدة البيانات: OpenAIRE
الوصف
تدمد:15206904
00223263