Self-Association and Nitroaromatic-Induced Deaggregation of Pyrene Substituted Pyridine Amides
DC Field | Value | Language |
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dc.contributor.author | Kim, Sung Kuk | - |
dc.contributor.author | Lim, Jong Min | - |
dc.contributor.author | Pradhan, Tuhin | - |
dc.contributor.author | Jung, Hyo Sung | - |
dc.contributor.author | Lynch, Vincent M. | - |
dc.contributor.author | Kim, Jong Seung | - |
dc.contributor.author | Kim, Dongho | - |
dc.contributor.author | Sesser, Jonathan L. | - |
dc.date.accessioned | 2021-09-05T12:24:03Z | - |
dc.date.available | 2021-09-05T12:24:03Z | - |
dc.date.created | 2021-06-15 | - |
dc.date.issued | 2014-01-08 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/99549 | - |
dc.description.abstract | The self-assembly features of the bis-pyrene methyl amide functionalized pyridine and benzene "tweezers" 1 and 2 were studied in organic solution and in the solid state. These systems were found to display remarkably different self-association features and optical properties, which was rationalized by control experiments using compounds bearing pyrenemethyl esters, alkyl groups, or a single pyrene substituent (3-6). As dilute solutions in chloroform, tweezers 1 displays both pyrene monomer and excimer emission features reflecting intramolecular contacts between the pyrene subunits. At higher concentrations in chloroform, as well as in the solid state, tweezers 1 self-assembles to form a linear supramolecular polymer. In contrast, tweezers 2 does not interact in an intermolecular fashion and photoexcitation produces emission features characteristic of a pyrene monomer. DFT (density functional theory) and TDDFT (time dependent density functional theory) calculations revealed that the lowest vertical transitions are forbidden and that S-1 of 1 is an emissive state. In contrast to 1 and 2, both pyrene-free control systems 5 and 6 were found to form linearly self-assembled supramolecular arrays in the solid state, albeit of differing structure. Upon exposure to trinitrobenzene (TNB), the self-assembled structures formed from 1 undergo deaggregation to form TNB complexes. This change is reflected in both an easily discernible color change and a quenching of the fluorescence emission intensity. Changes in the optical features were also seen in the case of 2. However, notable differences between these two ostensibly similar systems were seen. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | SUPRAMOLECULAR POLYMER CHEMISTRY | - |
dc.subject | MOLECULAR TWEEZERS | - |
dc.subject | SEQUENCE-RECOGNITION | - |
dc.subject | SYNTHETIC RECEPTORS | - |
dc.subject | LASER PHOTOLYSIS | - |
dc.subject | SHAPE-PERSISTENT | - |
dc.subject | HYDROGEN-BOND | - |
dc.subject | ACCEPTOR | - |
dc.subject | SENSORS | - |
dc.subject | DONOR | - |
dc.title | Self-Association and Nitroaromatic-Induced Deaggregation of Pyrene Substituted Pyridine Amides | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Kim, Jong Seung | - |
dc.identifier.doi | 10.1021/ja411672f | - |
dc.identifier.scopusid | 2-s2.0-84892178222 | - |
dc.identifier.wosid | 000329586600076 | - |
dc.identifier.bibliographicCitation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.136, no.1, pp.495 - 505 | - |
dc.relation.isPartOf | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.citation.title | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.citation.volume | 136 | - |
dc.citation.number | 1 | - |
dc.citation.startPage | 495 | - |
dc.citation.endPage | 505 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.subject.keywordPlus | SUPRAMOLECULAR POLYMER CHEMISTRY | - |
dc.subject.keywordPlus | MOLECULAR TWEEZERS | - |
dc.subject.keywordPlus | SEQUENCE-RECOGNITION | - |
dc.subject.keywordPlus | SYNTHETIC RECEPTORS | - |
dc.subject.keywordPlus | LASER PHOTOLYSIS | - |
dc.subject.keywordPlus | SHAPE-PERSISTENT | - |
dc.subject.keywordPlus | HYDROGEN-BOND | - |
dc.subject.keywordPlus | ACCEPTOR | - |
dc.subject.keywordPlus | SENSORS | - |
dc.subject.keywordPlus | DONOR | - |
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