Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene
A new deep-blue emitting and highly fluorescent anthracene (ANTH) derivative containing perfluorobenzyl (BnF) groups, 9,10-ANTH(BnF)2, was synthesized in a single step reaction of ANTH or ANTH(Br)2 with BnFI, using either a high-temperature Cu-/Na2S2O3-promoted reaction or via a room-temperature pho...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.39 |
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| author | Long K. San Sebastian Balser Brian J. Reeves Tyler T. Clikeman Yu-Sheng Chen Steven H. Strauss Olga V. Boltalina |
| author_facet | Long K. San Sebastian Balser Brian J. Reeves Tyler T. Clikeman Yu-Sheng Chen Steven H. Strauss Olga V. Boltalina |
| author_sort | Long K. San |
| collection | DOAJ |
| description | A new deep-blue emitting and highly fluorescent anthracene (ANTH) derivative containing perfluorobenzyl (BnF) groups, 9,10-ANTH(BnF)2, was synthesized in a single step reaction of ANTH or ANTH(Br)2 with BnFI, using either a high-temperature Cu-/Na2S2O3-promoted reaction or via a room-temperature photochemical reaction. Its structure was elucidated by NMR spectroscopy and single crystal X-ray diffractometry. The latter revealed no π–π interaction between neighboring ANTH cores. A combination of high photoluminescence quantum yield (PLQY) of 0.85 for 9,10-ANTH(BnF)2, its significantly improved photostability compared to ANTH and 9,10-ANTH derivatives, and a simple synthetic access makes it an attractive material as a deep-blue OLED emitter and an efficient fluorescent probe. |
| format | Article |
| id | doaj-art-aa86ee0b02b44ec5bdb185643470b25e |
| institution | OA Journals |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-aa86ee0b02b44ec5bdb185643470b25e2025-08-20T02:08:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-03-0121151552510.3762/bjoc.21.391860-5397-21-39Deep-blue emitting 9,10-bis(perfluorobenzyl)anthraceneLong K. San0Sebastian Balser1Brian J. Reeves2Tyler T. Clikeman3Yu-Sheng Chen4Steven H. Strauss5Olga V. Boltalina6Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA ChemMatCARS, University of Chicago Advanced Photon Source, Argonne, IL 60439, USA Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA A new deep-blue emitting and highly fluorescent anthracene (ANTH) derivative containing perfluorobenzyl (BnF) groups, 9,10-ANTH(BnF)2, was synthesized in a single step reaction of ANTH or ANTH(Br)2 with BnFI, using either a high-temperature Cu-/Na2S2O3-promoted reaction or via a room-temperature photochemical reaction. Its structure was elucidated by NMR spectroscopy and single crystal X-ray diffractometry. The latter revealed no π–π interaction between neighboring ANTH cores. A combination of high photoluminescence quantum yield (PLQY) of 0.85 for 9,10-ANTH(BnF)2, its significantly improved photostability compared to ANTH and 9,10-ANTH derivatives, and a simple synthetic access makes it an attractive material as a deep-blue OLED emitter and an efficient fluorescent probe.https://doi.org/10.3762/bjoc.21.39anthracenedibromoanthraceneelectron poor polyaromatic systemsfluorescenceperfluoroalkylationperfluorobenzylationphotochemistry |
| spellingShingle | Long K. San Sebastian Balser Brian J. Reeves Tyler T. Clikeman Yu-Sheng Chen Steven H. Strauss Olga V. Boltalina Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene Beilstein Journal of Organic Chemistry anthracene dibromoanthracene electron poor polyaromatic systems fluorescence perfluoroalkylation perfluorobenzylation photochemistry |
| title | Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene |
| title_full | Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene |
| title_fullStr | Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene |
| title_full_unstemmed | Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene |
| title_short | Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene |
| title_sort | deep blue emitting 9 10 bis perfluorobenzyl anthracene |
| topic | anthracene dibromoanthracene electron poor polyaromatic systems fluorescence perfluoroalkylation perfluorobenzylation photochemistry |
| url | https://doi.org/10.3762/bjoc.21.39 |
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