Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene
A set of novel 1,4-diaryl-1,3-butadiynes terminated by two 7-(arylethynyl)-1,8-bis(dimethylamino)naphthalene fragments was prepared via the Glaser–Hay oxidative dimerization of 2-ethynyl-7-(arylethynyl)-1,8-bis(dimethylamino)naphthalenes. The oligomers synthesized in this way are cross-conjugated sy...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2023-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.19.49 |
| _version_ | 1797809571026173952 |
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| author | Semyon V. Tsybulin Ekaterina A. Filatova Alexander F. Pozharskii Valery A. Ozeryanskii Anna V. Gulevskaya |
| author_facet | Semyon V. Tsybulin Ekaterina A. Filatova Alexander F. Pozharskii Valery A. Ozeryanskii Anna V. Gulevskaya |
| author_sort | Semyon V. Tsybulin |
| collection | DOAJ |
| description | A set of novel 1,4-diaryl-1,3-butadiynes terminated by two 7-(arylethynyl)-1,8-bis(dimethylamino)naphthalene fragments was prepared via the Glaser–Hay oxidative dimerization of 2-ethynyl-7-(arylethynyl)-1,8-bis(dimethylamino)naphthalenes. The oligomers synthesized in this way are cross-conjugated systems, in which two conjugation pathways are possible: π-conjugation of 1,8-bis(dimethylamino)naphthalene (DMAN) fragments through a butadiyne linker and a donor–acceptor aryl–C≡C–DMAN conjugation path. The conjugation path can be “switched” simply by protonation of DMAN fragments. X-ray diffraction, UV–vis spectroscopy and cyclic voltammetry are applied to analyze the extent of π-conjugation and the efficiency of particular donor–acceptor conjugation path in these new compounds. X-ray structures and absorption spectra of doubly protonated tetrafluoroborate salts of the oligomers are also discussed. |
| first_indexed | 2024-03-13T06:54:44Z |
| format | Article |
| id | doaj.art-4fd9fb8541674c4abdd70e5a3c594456 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-03-13T06:54:44Z |
| publishDate | 2023-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-4fd9fb8541674c4abdd70e5a3c5944562023-06-07T12:01:22ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972023-05-0119167468610.3762/bjoc.19.491860-5397-19-49Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthaleneSemyon V. Tsybulin0Ekaterina A. Filatova1Alexander F. Pozharskii2Valery A. Ozeryanskii3Anna V. Gulevskaya4Department of Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation Department of Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation Department of Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation Department of Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation Department of Chemistry, Southern Federal University, Zorge str. 7, Rostov-on-Don 344090, Russian Federation A set of novel 1,4-diaryl-1,3-butadiynes terminated by two 7-(arylethynyl)-1,8-bis(dimethylamino)naphthalene fragments was prepared via the Glaser–Hay oxidative dimerization of 2-ethynyl-7-(arylethynyl)-1,8-bis(dimethylamino)naphthalenes. The oligomers synthesized in this way are cross-conjugated systems, in which two conjugation pathways are possible: π-conjugation of 1,8-bis(dimethylamino)naphthalene (DMAN) fragments through a butadiyne linker and a donor–acceptor aryl–C≡C–DMAN conjugation path. The conjugation path can be “switched” simply by protonation of DMAN fragments. X-ray diffraction, UV–vis spectroscopy and cyclic voltammetry are applied to analyze the extent of π-conjugation and the efficiency of particular donor–acceptor conjugation path in these new compounds. X-ray structures and absorption spectra of doubly protonated tetrafluoroborate salts of the oligomers are also discussed.https://doi.org/10.3762/bjoc.19.491,8-bis(dimethylamino)naphthalenecross-conjugated systems1,4-diaryl-1,3-butadiynesdonor–acceptor systemsglaser–hay reaction |
| spellingShingle | Semyon V. Tsybulin Ekaterina A. Filatova Alexander F. Pozharskii Valery A. Ozeryanskii Anna V. Gulevskaya Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene Beilstein Journal of Organic Chemistry 1,8-bis(dimethylamino)naphthalene cross-conjugated systems 1,4-diaryl-1,3-butadiynes donor–acceptor systems glaser–hay reaction |
| title | Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene |
| title_full | Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene |
| title_fullStr | Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene |
| title_full_unstemmed | Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene |
| title_short | Synthesis, structure, and properties of switchable cross-conjugated 1,4-diaryl-1,3-butadiynes based on 1,8-bis(dimethylamino)naphthalene |
| title_sort | synthesis structure and properties of switchable cross conjugated 1 4 diaryl 1 3 butadiynes based on 1 8 bis dimethylamino naphthalene |
| topic | 1,8-bis(dimethylamino)naphthalene cross-conjugated systems 1,4-diaryl-1,3-butadiynes donor–acceptor systems glaser–hay reaction |
| url | https://doi.org/10.3762/bjoc.19.49 |
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