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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2013
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| Online Access: | 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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| _version_ | 1864513480152842240 |
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| author | Kaafarani, Bilal R. |
| author2 | El-Ballouli, Alaa O. Trattnig, Roman Fonari, Alexandr Sax, Stefan Wex, Brigitte Risko, Chad Khnayzer, Rony S. Barlow, Stephen Patra, Digambara Timofeeva, Tatiana V. |
| author2_role | author author author author author author author author author author |
| author_facet | Kaafarani, Bilal R. El-Ballouli, Alaa O. Trattnig, Roman Fonari, Alexandr Sax, Stefan Wex, Brigitte Risko, Chad Khnayzer, Rony S. Barlow, Stephen Patra, Digambara Timofeeva, Tatiana V. |
| author_role | author |
| dc.creator.none.fl_str_mv | Kaafarani, Bilal R. El-Ballouli, Alaa O. Trattnig, Roman Fonari, Alexandr Sax, Stefan Wex, Brigitte Risko, Chad Khnayzer, Rony S. Barlow, Stephen Patra, Digambara Timofeeva, Tatiana V. |
| dc.date.none.fl_str_mv | 2013 2017-11-03T07:35:03Z 2017-11-03T07:35:03Z 2017-11-03 |
| dc.identifier.none.fl_str_mv | 2050-7526 http://hdl.handle.net/10725/6491 http://dx.doi.org/10.1039/C2TC00474G Kaafarani, B. R., Ala'a, O., Trattnig, R., Fonari, A., Sax, S., Wex, B., ... & Timofeeva, T. V. (2013). Bis (carbazolyl) derivatives of pyrene and tetrahydropyrene: synthesis, structures, optical properties, electrochemistry, and electroluminescence. Journal of Materials Chemistry C, 1(8), 1638-1650. http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.php http://pubs.rsc.org/-/content/articlehtml/2013/tc/c2tc00474g |
| dc.language.none.fl_str_mv | en |
| dc.relation.none.fl_str_mv | Journal of Materials Chemistry C |
| dc.rights.*.fl_str_mv | info:eu-repo/semantics/openAccess |
| dc.title.none.fl_str_mv | Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene synthesis, structures, optical properties, electrochemistry, and electroluminescence |
| dc.type.none.fl_str_mv | Article info:eu-repo/semantics/publishedVersion info:eu-repo/semantics/article |
| description | 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. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | LAURepo_a91b957927beff4e6ef473e56d6b2ab1 |
| identifier_str_mv | 2050-7526 Kaafarani, B. R., Ala'a, O., Trattnig, R., Fonari, A., Sax, S., Wex, B., ... & Timofeeva, T. V. (2013). Bis (carbazolyl) derivatives of pyrene and tetrahydropyrene: synthesis, structures, optical properties, electrochemistry, and electroluminescence. Journal of Materials Chemistry C, 1(8), 1638-1650. |
| language_invalid_str_mv | en |
| network_acronym_str | LAURepo |
| network_name_str | Lebanese American University repository |
| oai_identifier_str | oai:laur.lau.edu.lb:10725/6491 |
| publishDate | 2013 |
| repository.mail.fl_str_mv | |
| repository.name.fl_str_mv | |
| repository_id_str | |
| spelling | Bis(carbazolyl) derivatives of pyrene and tetrahydropyrenesynthesis, structures, optical properties, electrochemistry, and electroluminescenceKaafarani, Bilal R.El-Ballouli, Alaa O.Trattnig, RomanFonari, AlexandrSax, StefanWex, BrigitteRisko, ChadKhnayzer, Rony S.Barlow, StephenPatra, DigambaraTimofeeva, Tatiana V.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.PublishedN/A2017-11-03T07:35:03Z2017-11-03T07:35:03Z20132017-11-03Articleinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article2050-7526http://hdl.handle.net/10725/6491http://dx.doi.org/10.1039/C2TC00474GKaafarani, B. R., Ala'a, O., Trattnig, R., Fonari, A., Sax, S., Wex, B., ... & Timofeeva, T. V. (2013). Bis (carbazolyl) derivatives of pyrene and tetrahydropyrene: synthesis, structures, optical properties, electrochemistry, and electroluminescence. Journal of Materials Chemistry C, 1(8), 1638-1650.http://libraries.lau.edu.lb/research/laur/terms-of-use/articles.phphttp://pubs.rsc.org/-/content/articlehtml/2013/tc/c2tc00474genJournal of Materials Chemistry Cinfo:eu-repo/semantics/openAccessoai:laur.lau.edu.lb:10725/64912021-03-19T10:03:26Z |
| spellingShingle | Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene Kaafarani, Bilal R. |
| status_str | publishedVersion |
| title | Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene |
| title_full | Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene |
| title_fullStr | Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene |
| title_full_unstemmed | Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene |
| title_short | Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene |
| title_sort | Bis(carbazolyl) derivatives of pyrene and tetrahydropyrene |
| url | 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 |