Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene

Tetrahydropyrene and pyrene have been functionalized in their 2,7-positions with carbazole and 3,6-di-tert-butylcarbazole groups, and the properties of these new compounds are compared to analogous carbazole and 3,6-di-tert-butylcarbazole derivatives of benzene and biphenyl using X-ray crystallograp...

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محفوظ في:
التفاصيل البيبلوغرافية
المؤلف الرئيسي: Kaafarani, Bilal R. (author)
مؤلفون آخرون: El-Ballouli, Alaa O. (author), Trattnig, Roman (author), Fonari, Alexandr (author), Sax, Stefan (author), Wex, Brigitte (author), Risko, Chad (author), Khnayzer, Rony S. (author), Barlow, Stephen (author), Patra, Digambara (author), Timofeeva, Tatiana V. (author)
التنسيق: article
منشور في: 2013
الوصول للمادة أونلاين:http://hdl.handle.net/10725/6491
http://dx.doi.org/10.1039/C2TC00474G
http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php
http://pubs.rsc.org/-/content/articlehtml/2013/tc/c2tc00474g
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الوصف
الملخص:Tetrahydropyrene and pyrene have been functionalized in their 2,7-positions with carbazole and 3,6-di-tert-butylcarbazole groups, and the properties of these new compounds are compared to analogous carbazole and 3,6-di-tert-butylcarbazole derivatives of benzene and biphenyl using X-ray crystallography, UV-vis absorption and fluorescence spectroscopy, electrochemistry, and quantum-chemical calculations. The absorption spectra are similar to those of their biphenyl-bridged analogues, although TD-DFT calculations indicate a different description of the excited states in the pyrene case, with the lowest observed absorption no longer corresponding to the S0 → S1 transition. The 3,6-di-tert-butylcarbazole compounds show reversible electrochemical oxidations; the benzene, biphenyl, tetrahydropyrene, or pyrene bridging groups have little impact on the first oxidation potential. Bilayer organic light-emitting diodes incorporating the tetrahydropyrene and pyrene derivatives as emitters show deep-blue electroluminescence.