Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene
A series of BN-phenanthrenes with substituents of a diverse nature have been synthesized by palladium-catalyzed cross-coupling reactions of a common chloro-substituted precursor, which was made from readily available materials in only four steps. Evaluation of the photophysical properties of the pre...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2019-06-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.15.122 |
| _version_ | 1818954252021661696 |
|---|---|
| author | Alberto Abengózar David Sucunza Patricia García-García Juan J. Vaquero |
| author_facet | Alberto Abengózar David Sucunza Patricia García-García Juan J. Vaquero |
| author_sort | Alberto Abengózar |
| collection | DOAJ |
| description | A series of BN-phenanthrenes with substituents of a diverse nature have been synthesized by palladium-catalyzed cross-coupling reactions of a common chloro-substituted precursor, which was made from readily available materials in only four steps. Evaluation of the photophysical properties of the prepared compounds unveiled an impressive effect of the presence of alkynyl substituents on the fluorescence quantum yield, which improved from 0.01 in the parent compound to up to 0.65 in derivatives containing a triple bond. |
| first_indexed | 2024-12-20T10:19:12Z |
| format | Article |
| id | doaj.art-e672eeb4fb8d4f10a6b8fb43fc28313c |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T10:19:12Z |
| publishDate | 2019-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-e672eeb4fb8d4f10a6b8fb43fc28313c2022-12-21T19:43:58ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-06-011511257126110.3762/bjoc.15.1221860-5397-15-122Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthreneAlberto Abengózar0David Sucunza1Patricia García-García2Juan J. Vaquero3Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química “Andrés M. del Río” (IQAR), Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, SpainDepartamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química “Andrés M. del Río” (IQAR), Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, SpainDepartamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química “Andrés M. del Río” (IQAR), Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, SpainDepartamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química “Andrés M. del Río” (IQAR), Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, SpainA series of BN-phenanthrenes with substituents of a diverse nature have been synthesized by palladium-catalyzed cross-coupling reactions of a common chloro-substituted precursor, which was made from readily available materials in only four steps. Evaluation of the photophysical properties of the prepared compounds unveiled an impressive effect of the presence of alkynyl substituents on the fluorescence quantum yield, which improved from 0.01 in the parent compound to up to 0.65 in derivatives containing a triple bond.https://doi.org/10.3762/bjoc.15.122alkyneBN-phenanthrenecross-couplingfluorescenceheterocycles |
| spellingShingle | Alberto Abengózar David Sucunza Patricia García-García Juan J. Vaquero Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene Beilstein Journal of Organic Chemistry alkyne BN-phenanthrene cross-coupling fluorescence heterocycles |
| title | Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene |
| title_full | Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene |
| title_fullStr | Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene |
| title_full_unstemmed | Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene |
| title_short | Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene |
| title_sort | remarkable effect of alkynyl substituents on the fluorescence properties of a bn phenanthrene |
| topic | alkyne BN-phenanthrene cross-coupling fluorescence heterocycles |
| url | https://doi.org/10.3762/bjoc.15.122 |
| work_keys_str_mv | AT albertoabengozar remarkableeffectofalkynylsubstituentsonthefluorescencepropertiesofabnphenanthrene AT davidsucunza remarkableeffectofalkynylsubstituentsonthefluorescencepropertiesofabnphenanthrene AT patriciagarciagarcia remarkableeffectofalkynylsubstituentsonthefluorescencepropertiesofabnphenanthrene AT juanjvaquero remarkableeffectofalkynylsubstituentsonthefluorescencepropertiesofabnphenanthrene |