4-Arylvinyl-2,6-di(pyridin-2-yl)pyrimidines: Synthesis and Optical Properties
A series of 4-arylvinyl-2,6-di(pyridin-2-yl)pyrimidines have been efficiently prepared by a double cross-coupling reaction between 2,4-dichloro-6-methylpyrimidine and 2-(tributylstannyl)pyridine, followed by aldol condensation with the appropriate aromatic aldehyde substituted with electron-donating...
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| Veröffentlicht in: | Journal of organic chemistry 2011-05, Vol.76 (10), p.3837-3845 |
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| container_issue | 10 |
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| container_title | Journal of organic chemistry |
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| creator | Hadad, Caroline Achelle, Sylvain García-Martinez, Joaquín C Rodríguez-López, Julián |
| description | A series of 4-arylvinyl-2,6-di(pyridin-2-yl)pyrimidines have been efficiently prepared by a double cross-coupling reaction between 2,4-dichloro-6-methylpyrimidine and 2-(tributylstannyl)pyridine, followed by aldol condensation with the appropriate aromatic aldehyde substituted with electron-donating, electron-withdrawing, dendritic, or water-soluble groups. The effect of different protic and aprotic solvents on the optical absorption and emission properties of these systems was studied. Compounds with electron-donating groups display strong emission solvatochromism, suggesting the formation of an intramolecular charge-separated emitting state. The solvatochromic behavior depends not only on the solvent polarity but also on the hydrogen bonding parameters of the solvent. The effect of protonation was also studied, and the abilities of some of these molecules to function as colorimetric and luminescent pH sensors were demonstrated with dramatic color changes and luminescence switching upon the introduction of acid. |
| doi_str_mv | 10.1021/jo200204u |
| format | Article |
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The effect of different protic and aprotic solvents on the optical absorption and emission properties of these systems was studied. Compounds with electron-donating groups display strong emission solvatochromism, suggesting the formation of an intramolecular charge-separated emitting state. The solvatochromic behavior depends not only on the solvent polarity but also on the hydrogen bonding parameters of the solvent. 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Org. Chem</addtitle><description>A series of 4-arylvinyl-2,6-di(pyridin-2-yl)pyrimidines have been efficiently prepared by a double cross-coupling reaction between 2,4-dichloro-6-methylpyrimidine and 2-(tributylstannyl)pyridine, followed by aldol condensation with the appropriate aromatic aldehyde substituted with electron-donating, electron-withdrawing, dendritic, or water-soluble groups. The effect of different protic and aprotic solvents on the optical absorption and emission properties of these systems was studied. Compounds with electron-donating groups display strong emission solvatochromism, suggesting the formation of an intramolecular charge-separated emitting state. The solvatochromic behavior depends not only on the solvent polarity but also on the hydrogen bonding parameters of the solvent. 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Org. Chem</addtitle><date>2011-05-20</date><risdate>2011</risdate><volume>76</volume><issue>10</issue><spage>3837</spage><epage>3845</epage><pages>3837-3845</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A series of 4-arylvinyl-2,6-di(pyridin-2-yl)pyrimidines have been efficiently prepared by a double cross-coupling reaction between 2,4-dichloro-6-methylpyrimidine and 2-(tributylstannyl)pyridine, followed by aldol condensation with the appropriate aromatic aldehyde substituted with electron-donating, electron-withdrawing, dendritic, or water-soluble groups. The effect of different protic and aprotic solvents on the optical absorption and emission properties of these systems was studied. Compounds with electron-donating groups display strong emission solvatochromism, suggesting the formation of an intramolecular charge-separated emitting state. The solvatochromic behavior depends not only on the solvent polarity but also on the hydrogen bonding parameters of the solvent. The effect of protonation was also studied, and the abilities of some of these molecules to function as colorimetric and luminescent pH sensors were demonstrated with dramatic color changes and luminescence switching upon the introduction of acid.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>21462944</pmid><doi>10.1021/jo200204u</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-9226-7735</orcidid></addata></record> |
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| source | ACS Publications |
| subjects | Applied sciences Chemical Sciences Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Organic polymers Physicochemistry of polymers Polymers with particular structures Preparation, kinetics, thermodynamics, mechanism and catalysts Preparations and properties |
| title | 4-Arylvinyl-2,6-di(pyridin-2-yl)pyrimidines: Synthesis and Optical Properties |
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