Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure Thereof
The synthesis of multiply substituted acenes is still a relevant research problem, considering their applications and future potential. Here we present an elegant synthetic protocol to afford tetra-peri-substituted naphthalene and tetracene from their tetrahalo derivatives by a Pd(0)-catalyzed C-C c...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/13/5074 |
| _version_ | 1827734689747566592 |
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| author | Gayathri Jothish Kumar Benny Bogoslavsky Sashi Debnath Anjan Bedi |
| author_facet | Gayathri Jothish Kumar Benny Bogoslavsky Sashi Debnath Anjan Bedi |
| author_sort | Gayathri Jothish Kumar |
| collection | DOAJ |
| description | The synthesis of multiply substituted acenes is still a relevant research problem, considering their applications and future potential. Here we present an elegant synthetic protocol to afford tetra-peri-substituted naphthalene and tetracene from their tetrahalo derivatives by a Pd(0)-catalyzed C-C cross-coupling method in a single step. The newly synthesized tetracenes were characterized by NMR, HRMS, UV-vis spectrophotometry, and single-crystal X-ray diffraction (SCXRD). In addition, the first systematic computational study of the effect of chalcogenophenyl substitutions on the chiroptical properties of twistacenes was reported here. The gas phase computational studies using density functional theory (DFT) on a series of chalcogenophene-substituted tetracenes revealed that their chiroptical activity could be systematically increased via the atomistic tuning of peripheral substituents. |
| first_indexed | 2024-03-11T01:33:57Z |
| format | Article |
| id | doaj.art-31b5fb1da6cf438786209c13b1e139f4 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T01:33:57Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-31b5fb1da6cf438786209c13b1e139f42023-11-18T17:07:48ZengMDPI AGMolecules1420-30492023-06-012813507410.3390/molecules28135074Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure ThereofGayathri Jothish Kumar0Benny Bogoslavsky1Sashi Debnath2Anjan Bedi3Department of Chemistry, SRM Institute of Science and Technology, Kattankulathur, Chennai 603203, IndiaInstitute of Chemistry, The Hebrew University of Jerusalem, Edmond J. Safra Campus, Jerusalem 91904, IsraelDepartment of Radiology, University of Texas Southwestern Medical Center, Dallas, TX 75390, USADepartment of Chemistry, SRM Institute of Science and Technology, Kattankulathur, Chennai 603203, IndiaThe synthesis of multiply substituted acenes is still a relevant research problem, considering their applications and future potential. Here we present an elegant synthetic protocol to afford tetra-peri-substituted naphthalene and tetracene from their tetrahalo derivatives by a Pd(0)-catalyzed C-C cross-coupling method in a single step. The newly synthesized tetracenes were characterized by NMR, HRMS, UV-vis spectrophotometry, and single-crystal X-ray diffraction (SCXRD). In addition, the first systematic computational study of the effect of chalcogenophenyl substitutions on the chiroptical properties of twistacenes was reported here. The gas phase computational studies using density functional theory (DFT) on a series of chalcogenophene-substituted tetracenes revealed that their chiroptical activity could be systematically increased via the atomistic tuning of peripheral substituents.https://www.mdpi.com/1420-3049/28/13/5074tetracenechalcogenopheneSuzuki couplingtwisted aceneschiroptical properties |
| spellingShingle | Gayathri Jothish Kumar Benny Bogoslavsky Sashi Debnath Anjan Bedi Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure Thereof Molecules tetracene chalcogenophene Suzuki coupling twisted acenes chiroptical properties |
| title | Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure Thereof |
| title_full | Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure Thereof |
| title_fullStr | Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure Thereof |
| title_full_unstemmed | Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure Thereof |
| title_short | Effect of Chalcogenophenes on Chiroptical Activity of Twisted Tetracenes: Computational Analysis, Synthesis and Crystal Structure Thereof |
| title_sort | effect of chalcogenophenes on chiroptical activity of twisted tetracenes computational analysis synthesis and crystal structure thereof |
| topic | tetracene chalcogenophene Suzuki coupling twisted acenes chiroptical properties |
| url | https://www.mdpi.com/1420-3049/28/13/5074 |
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