DC Field | Value | Language |
---|---|---|
dc.contributor.author | Lee, Ju Young | ko |
dc.contributor.author | Shim, Jae Yul | ko |
dc.contributor.author | Kim, Hongki | ko |
dc.contributor.author | Ko, Donguk | ko |
dc.contributor.author | Baik, Mu-Hyun | ko |
dc.contributor.author | Yoo, Eun Jeong | ko |
dc.date.accessioned | 2017-06-05T02:20:42Z | - |
dc.date.available | 2017-06-05T02:20:42Z | - |
dc.date.created | 2017-05-29 | - |
dc.date.created | 2017-05-29 | - |
dc.date.issued | 2017-04 | - |
dc.identifier.citation | JOURNAL OF ORGANIC CHEMISTRY, v.82, no.8, pp.4352 - 4361 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10203/223916 | - |
dc.description.abstract | A new protocol for the synthesis of color-tunable fluorescent 3,S-diarylimidazo[1,2-a]pyridines has been achieved via palladium-catalyzed C H amination of pyridinium zwitterions. Based on experimental, results and computational analysis, we extracted a high correlation of photophysical properties with the theoretical concept and predicted emission wavelengths of 3,5diarylimidazo [1,2-a]pyridines. The emission wavelengths of imidazo[1,2-a]pyridines increase as a function of the electron withdrawing nature of the substituent on the CS-aryl group of imidazo[1,2-a]pyridine as a result of inductive effects on the LUMO levels. Varying the substituent on the C3-aryl group imidazo[1,2-a]pyridine changes the HOMO levels. Combining these two sites, the HOMO and LUMO levels can be tuned fairly decoupled from each other. This conceptual trend is demonstrated across a series where the C3 and CS positions were functionalized independently and then utilizes a combination strategy where both sites are used to prepare fluorophores with a large window of emission wavelengths. In view of the biological properties of imidazo[1,2-a]pyridines, the developed method provides an efficient approach for understanding and preparing strongly fluorescent bioprobes. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | ONE-POT SYNTHESIS | - |
dc.subject | C-H AMINATION | - |
dc.subject | DENSITY-FUNCTIONAL THEORY | - |
dc.subject | EFFECTIVE CORE POTENTIALS | - |
dc.subject | SOLVATION FREE-ENERGIES | - |
dc.subject | MOLECULAR CALCULATIONS | - |
dc.subject | COMBINATORIAL DISCOVERY | - |
dc.subject | CYCLOADDITION REACTIONS | - |
dc.subject | COUPLING REACTIONS | - |
dc.subject | AZOMETHINE YLIDES | - |
dc.title | 3,5-Diarylimidazo[1,2-a]pyridines as Color-Tunable Fluorophores | - |
dc.type | Article | - |
dc.identifier.wosid | 000400124100033 | - |
dc.identifier.scopusid | 2-s2.0-85018488057 | - |
dc.type.rims | ART | - |
dc.citation.volume | 82 | - |
dc.citation.issue | 8 | - |
dc.citation.beginningpage | 4352 | - |
dc.citation.endingpage | 4361 | - |
dc.citation.publicationname | JOURNAL OF ORGANIC CHEMISTRY | - |
dc.identifier.doi | 10.1021/acs.joc.7b00358 | - |
dc.contributor.localauthor | Baik, Mu-Hyun | - |
dc.contributor.nonIdAuthor | Lee, Ju Young | - |
dc.contributor.nonIdAuthor | Shim, Jae Yul | - |
dc.contributor.nonIdAuthor | Ko, Donguk | - |
dc.contributor.nonIdAuthor | Yoo, Eun Jeong | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | ONE-POT SYNTHESIS | - |
dc.subject.keywordPlus | C-H AMINATION | - |
dc.subject.keywordPlus | DENSITY-FUNCTIONAL THEORY | - |
dc.subject.keywordPlus | EFFECTIVE CORE POTENTIALS | - |
dc.subject.keywordPlus | SOLVATION FREE-ENERGIES | - |
dc.subject.keywordPlus | MOLECULAR CALCULATIONS | - |
dc.subject.keywordPlus | COMBINATORIAL DISCOVERY | - |
dc.subject.keywordPlus | CYCLOADDITION REACTIONS | - |
dc.subject.keywordPlus | COUPLING REACTIONS | - |
dc.subject.keywordPlus | AZOMETHINE YLIDES | - |
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