Thiophene-based covalent organic frameworks
We report the synthesis and characterization of covalent organic frameworks (COFs) incorporating thiophene-based building blocks. We show that these are amenable to reticular synthesis, and that bent ditopic monomers, such as 2,5-thiophenediboronic acid, are defect-prone building blocks that are sus...
Principais autores: | , , , , |
---|---|
Outros Autores: | |
Formato: | Artigo |
Idioma: | en_US |
Publicado em: |
National Academy of Sciences (U.S.)
2013
|
Acesso em linha: | http://hdl.handle.net/1721.1/81293 https://orcid.org/0000-0003-1589-832X https://orcid.org/0000-0002-1262-1264 https://orcid.org/0000-0002-6708-7660 |
_version_ | 1826214914289565696 |
---|---|
author | Bertrand, Guillaume Michaelis, Vladimir K. Ong, Ta-Chung Griffin, Robert Guy Dinca, Mircea |
author2 | Massachusetts Institute of Technology. Department of Chemistry |
author_facet | Massachusetts Institute of Technology. Department of Chemistry Bertrand, Guillaume Michaelis, Vladimir K. Ong, Ta-Chung Griffin, Robert Guy Dinca, Mircea |
author_sort | Bertrand, Guillaume |
collection | MIT |
description | We report the synthesis and characterization of covalent organic frameworks (COFs) incorporating thiophene-based building blocks. We show that these are amenable to reticular synthesis, and that bent ditopic monomers, such as 2,5-thiophenediboronic acid, are defect-prone building blocks that are susceptible to synthetic variations during COF synthesis. The synthesis and characterization of an unusual charge transfer complex between thieno[3,2-b]thiophene-2,5-diboronic acid and tetracyanoquinodimethane enabled by the unique COF architecture is also presented. Together, these results delineate important synthetic advances toward the implementation of COFs in electronic devices. |
first_indexed | 2024-09-23T16:12:45Z |
format | Article |
id | mit-1721.1/81293 |
institution | Massachusetts Institute of Technology |
language | en_US |
last_indexed | 2024-09-23T16:12:45Z |
publishDate | 2013 |
publisher | National Academy of Sciences (U.S.) |
record_format | dspace |
spelling | mit-1721.1/812932022-09-29T18:57:16Z Thiophene-based covalent organic frameworks Bertrand, Guillaume Michaelis, Vladimir K. Ong, Ta-Chung Griffin, Robert Guy Dinca, Mircea Massachusetts Institute of Technology. Department of Chemistry Francis Bitter Magnet Laboratory (Massachusetts Institute of Technology) Bertrand, Guillaume Michaelis, Vladimir K. Ong, Ta-Chung Griffin, Robert Guy Dinca, Mircea We report the synthesis and characterization of covalent organic frameworks (COFs) incorporating thiophene-based building blocks. We show that these are amenable to reticular synthesis, and that bent ditopic monomers, such as 2,5-thiophenediboronic acid, are defect-prone building blocks that are susceptible to synthetic variations during COF synthesis. The synthesis and characterization of an unusual charge transfer complex between thieno[3,2-b]thiophene-2,5-diboronic acid and tetracyanoquinodimethane enabled by the unique COF architecture is also presented. Together, these results delineate important synthetic advances toward the implementation of COFs in electronic devices. United States. Dept. of Energy. Office of Basic Energy Sciences (Award DE-SC0006937) National Institutes of Health (U.S.) (Grant EB001960) National Institutes of Health (U.S.) (Grant EB002026) 2013-10-03T17:12:50Z 2013-10-03T17:12:50Z 2013-03 2012-12 Article http://purl.org/eprint/type/JournalArticle 0027-8424 1091-6490 http://hdl.handle.net/1721.1/81293 Bertrand, G. H. V., V. K. Michaelis, T.-C. Ong, R. G. Griffin, and M. Dinca. “Thiophene-based covalent organic frameworks.” Proceedings of the National Academy of Sciences 110, no. 13 (March 26, 2013): 4923-4928. https://orcid.org/0000-0003-1589-832X https://orcid.org/0000-0002-1262-1264 https://orcid.org/0000-0002-6708-7660 en_US http://dx.doi.org/10.1073/pnas.1221824110 Proceedings of the National Academy of Sciences Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf National Academy of Sciences (U.S.) PNAS |
spellingShingle | Bertrand, Guillaume Michaelis, Vladimir K. Ong, Ta-Chung Griffin, Robert Guy Dinca, Mircea Thiophene-based covalent organic frameworks |
title | Thiophene-based covalent organic frameworks |
title_full | Thiophene-based covalent organic frameworks |
title_fullStr | Thiophene-based covalent organic frameworks |
title_full_unstemmed | Thiophene-based covalent organic frameworks |
title_short | Thiophene-based covalent organic frameworks |
title_sort | thiophene based covalent organic frameworks |
url | http://hdl.handle.net/1721.1/81293 https://orcid.org/0000-0003-1589-832X https://orcid.org/0000-0002-1262-1264 https://orcid.org/0000-0002-6708-7660 |
work_keys_str_mv | AT bertrandguillaume thiophenebasedcovalentorganicframeworks AT michaelisvladimirk thiophenebasedcovalentorganicframeworks AT ongtachung thiophenebasedcovalentorganicframeworks AT griffinrobertguy thiophenebasedcovalentorganicframeworks AT dincamircea thiophenebasedcovalentorganicframeworks |