TTFs nonsymmetrically fused with alkylthiophenic moieties
Two new dithiolene ligand precursors, containing fused TTF and alkyl thiophenic moieties 3,3'-{[2-(5-(tert-butyl)thieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-tbtdt, 1), and 3,3'-{[2-(5-methylthieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiol...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2015-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.11.71 |
| _version_ | 1818933768135639040 |
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| author | Rafaela A. L. Silva Bruno J. C. Vieira Marta M. Andrade Isabel C. Santos Sandra Rabaça Dulce Belo Manuel Almeida |
| author_facet | Rafaela A. L. Silva Bruno J. C. Vieira Marta M. Andrade Isabel C. Santos Sandra Rabaça Dulce Belo Manuel Almeida |
| author_sort | Rafaela A. L. Silva |
| collection | DOAJ |
| description | Two new dithiolene ligand precursors, containing fused TTF and alkyl thiophenic moieties 3,3'-{[2-(5-(tert-butyl)thieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-tbtdt, 1), and 3,3'-{[2-(5-methylthieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-mtdt, 2), were synthesized and characterized. The electrochemical properties of these electronic donors were studied by cyclic voltammetry (CV) in dichloromethane. Both compounds show two quasi-reversible oxidation processes, versus Ag/AgCl, typical of TTF donors at E11/2 = 279 V and E21/2 = 680 V for 1 and E11/2 = 304 V and E21/2 = 716 V in the case of 2. The single-crystal X-ray structure of 1 and of a charge transfer salt of 2, (α-mtdt)[Au(mnt)2] (3), are reported. |
| first_indexed | 2024-12-20T04:53:37Z |
| format | Article |
| id | doaj.art-cc6a52dfd05d4fe5945666272fabebca |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T04:53:37Z |
| publishDate | 2015-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-cc6a52dfd05d4fe5945666272fabebca2022-12-21T19:52:48ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-05-0111162863710.3762/bjoc.11.711860-5397-11-71TTFs nonsymmetrically fused with alkylthiophenic moietiesRafaela A. L. Silva0Bruno J. C. Vieira1Marta M. Andrade2Isabel C. Santos3Sandra Rabaça4Dulce Belo5Manuel Almeida6Centro de Ciências e Tecnologias Nucleares, Campus Tecnológico e Nuclear, Instituto Superior Técnico, Universidade de Lisboa, Estrada Nacional 10, ao km 139,7, 2695-066 Bobadela LRS, PortugalCentro de Ciências e Tecnologias Nucleares, Campus Tecnológico e Nuclear, Instituto Superior Técnico, Universidade de Lisboa, Estrada Nacional 10, ao km 139,7, 2695-066 Bobadela LRS, PortugalCentro de Ciências e Tecnologias Nucleares, Campus Tecnológico e Nuclear, Instituto Superior Técnico, Universidade de Lisboa, Estrada Nacional 10, ao km 139,7, 2695-066 Bobadela LRS, PortugalCentro de Ciências e Tecnologias Nucleares, Campus Tecnológico e Nuclear, Instituto Superior Técnico, Universidade de Lisboa, Estrada Nacional 10, ao km 139,7, 2695-066 Bobadela LRS, PortugalCentro de Ciências e Tecnologias Nucleares, Campus Tecnológico e Nuclear, Instituto Superior Técnico, Universidade de Lisboa, Estrada Nacional 10, ao km 139,7, 2695-066 Bobadela LRS, PortugalCentro de Ciências e Tecnologias Nucleares, Campus Tecnológico e Nuclear, Instituto Superior Técnico, Universidade de Lisboa, Estrada Nacional 10, ao km 139,7, 2695-066 Bobadela LRS, PortugalCentro de Ciências e Tecnologias Nucleares, Campus Tecnológico e Nuclear, Instituto Superior Técnico, Universidade de Lisboa, Estrada Nacional 10, ao km 139,7, 2695-066 Bobadela LRS, PortugalTwo new dithiolene ligand precursors, containing fused TTF and alkyl thiophenic moieties 3,3'-{[2-(5-(tert-butyl)thieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-tbtdt, 1), and 3,3'-{[2-(5-methylthieno[2,3-d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-diyl]bis[sulfanediyl]}dipropanenitrile (α-mtdt, 2), were synthesized and characterized. The electrochemical properties of these electronic donors were studied by cyclic voltammetry (CV) in dichloromethane. Both compounds show two quasi-reversible oxidation processes, versus Ag/AgCl, typical of TTF donors at E11/2 = 279 V and E21/2 = 680 V for 1 and E11/2 = 304 V and E21/2 = 716 V in the case of 2. The single-crystal X-ray structure of 1 and of a charge transfer salt of 2, (α-mtdt)[Au(mnt)2] (3), are reported.https://doi.org/10.3762/bjoc.11.71cyclic voltammetrysingle-crystal X-ray diffractionsupramolecular chemistrytetrathiafulvalene (TTF)thiophene |
| spellingShingle | Rafaela A. L. Silva Bruno J. C. Vieira Marta M. Andrade Isabel C. Santos Sandra Rabaça Dulce Belo Manuel Almeida TTFs nonsymmetrically fused with alkylthiophenic moieties Beilstein Journal of Organic Chemistry cyclic voltammetry single-crystal X-ray diffraction supramolecular chemistry tetrathiafulvalene (TTF) thiophene |
| title | TTFs nonsymmetrically fused with alkylthiophenic moieties |
| title_full | TTFs nonsymmetrically fused with alkylthiophenic moieties |
| title_fullStr | TTFs nonsymmetrically fused with alkylthiophenic moieties |
| title_full_unstemmed | TTFs nonsymmetrically fused with alkylthiophenic moieties |
| title_short | TTFs nonsymmetrically fused with alkylthiophenic moieties |
| title_sort | ttfs nonsymmetrically fused with alkylthiophenic moieties |
| topic | cyclic voltammetry single-crystal X-ray diffraction supramolecular chemistry tetrathiafulvalene (TTF) thiophene |
| url | https://doi.org/10.3762/bjoc.11.71 |
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