DC Field | Value | Language |
---|---|---|
dc.contributor.author | Do, Young-Kyu | ko |
dc.contributor.author | Churchill, David G | ko |
dc.contributor.author | Choi, Shin-Hei | ko |
dc.contributor.author | Kim, Ki-Bong | ko |
dc.contributor.author | Lee, Jun-Seong | ko |
dc.date.accessioned | 2009-09-03T08:55:33Z | - |
dc.date.available | 2009-09-03T08:55:33Z | - |
dc.date.created | 2012-02-06 | - |
dc.date.created | 2012-02-06 | - |
dc.date.issued | 2007-05 | - |
dc.identifier.citation | JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, v.37, no.5, pp.315 - 331 | - |
dc.identifier.issn | 1074-1542 | - |
dc.identifier.uri | http://hdl.handle.net/10203/10976 | - |
dc.description.abstract | To explore the characteristics of potential fluorescent probes that could be used to screen prospective HDS catalysts, new 5-thienyl dipyrromethene derivatives have been prepared. 5-(2-thienyl)- (1a), 5-(3-thienyl)- (1b), and 5-(3-(2,5-dibromothienyl))-dipyrromethane (1c), were oxidized with DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) separately to give the corresponding dipyrrins 2a-2c. These were subsequently treated with F3B center dot OEt2 to afford the respective N,N'-difluoroboryl-5-(thienyl)dipyrrin compounds, 3a-3c; the latter two may serve as polymer precursors. Significant fluorescence signal enhancement is achieved with 3a-3c over 2a-2c. Orange fluorescence is observed for 3a whereas its isomer 3b gives green fluorescence (365 nm). An X-ray diffraction study of 3a was performed (orthorhombic, P2(1)2(1)2(1), a=10.684(10) angstrom, b=15.208(13) angstrom, c=7.256(6) angstrom, V=1179.0(17) angstrom(3), Z=4, R (1)=0.0428, wR (2)=0.0686) and its geometry was studied by way of DFT (Gaussian 03; B3LYP/6-31G*) to give a HOMO/LUMO energy level difference of 414 nm, and a 2-thienyl group rotational barrier of similar to 6 kcal/mol, compared to that of similar to 12 kcal/mol for the phenyl derivative. Theoretical modeling of 2a demonstrated that the [N-H center dot center dot center dot N] interaction is favored by ca. 10 kcal/mol, whereas [N-H center dot center dot center dot S] bonding is sterically unattainable. | - |
dc.description.sponsorship | financial support from KAIST, the CMDS, the BK 21 Project and the KRF (Korea Research Foundation) | en |
dc.language | English | - |
dc.language.iso | en_US | en |
dc.publisher | SPRINGER/PLENUM PUBLISHERS | - |
dc.subject | C-S BOND | - |
dc.subject | HOMOGENEOUS HYDRODESULFURIZATION | - |
dc.subject | SUBSTITUTED THIOPHENES | - |
dc.subject | BODIPY DYES | - |
dc.subject | CLEAVAGE | - |
dc.subject | TRIS(TRIETHYLPHOSPHINE)PLATINUM(0) | - |
dc.subject | POLYTHIOPHENES | - |
dc.subject | REACTIVITY | - |
dc.subject | COMPLEXES | - |
dc.subject | INSERTION | - |
dc.title | X-ray diffraction, DFT, and spectroscopic study of N,N -difluoroboryl-5-(2-thienyl)dipyrrin and fluorescence studies of related dipyrromethanes, dipyrrins and BF2-dipyrrins and DFT conformational study of 5-(2-thienyl)dipyrrin | - |
dc.type | Article | - |
dc.identifier.wosid | 000245106000001 | - |
dc.identifier.scopusid | 2-s2.0-33947404035 | - |
dc.type.rims | ART | - |
dc.citation.volume | 37 | - |
dc.citation.issue | 5 | - |
dc.citation.beginningpage | 315 | - |
dc.citation.endingpage | 331 | - |
dc.citation.publicationname | JOURNAL OF CHEMICAL CRYSTALLOGRAPHY | - |
dc.identifier.doi | 10.1007/s10870-006-9126-0 | - |
dc.embargo.liftdate | 9999-12-31 | - |
dc.embargo.terms | 9999-12-31 | - |
dc.contributor.localauthor | Do, Young-Kyu | - |
dc.contributor.localauthor | Churchill, David G | - |
dc.contributor.nonIdAuthor | Choi, Shin-Hei | - |
dc.contributor.nonIdAuthor | Lee, Jun-Seong | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | thienyl | - |
dc.subject.keywordAuthor | difluoroboryl-dipyrrin | - |
dc.subject.keywordAuthor | crystal structure | - |
dc.subject.keywordAuthor | DFT calculation | - |
dc.subject.keywordAuthor | fluorescence | - |
dc.subject.keywordPlus | C-S BOND | - |
dc.subject.keywordPlus | HOMOGENEOUS HYDRODESULFURIZATION | - |
dc.subject.keywordPlus | SUBSTITUTED THIOPHENES | - |
dc.subject.keywordPlus | BODIPY DYES | - |
dc.subject.keywordPlus | CLEAVAGE | - |
dc.subject.keywordPlus | TRIS(TRIETHYLPHOSPHINE)PLATINUM(0) | - |
dc.subject.keywordPlus | POLYTHIOPHENES | - |
dc.subject.keywordPlus | REACTIVITY | - |
dc.subject.keywordPlus | COMPLEXES | - |
dc.subject.keywordPlus | INSERTION | - |
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