Diastereomeric isomerization of hetaryl leuco-TAM dyes, (2Z, 2′E)-2,2′-(2-phenyl propane-1,3-diylidene)bis(1,3,3-trimethylindoline) derivatives in various organic solvents |
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Authors: | Sam-Rok Keum Se-Jung Roh Do-Kyung Kim |
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Institution: | a Department of Advanced Material Chemistry, Korea University, Jochiwon 339-700, South Korea b Department of Biotechnology and Bioinformatics, Korea University, Jochiwon 339-700, South Korea |
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Abstract: | The diastereomeric isomerization of the ZE isomers of (2Z, 2′E)-2,2′-(2-phenyl propane-1,3-diylidene) bis(1,3,3-trimethylindoline) derivatives were examined by 1H NMR spectroscopy in various organic solvents. In non-polar solvents, such as benzene, THF, and chloroform, the ZE isomers of these molecules equilibrated into a mixture of ZE/EE or ZE/EE/ZZ isomers with time, whereas the isomers were inert in polar organic solvents, such as acetone and DMSO. Theoretical calculations of the energies and dipole moments of the diastereomers in different media were performed using the Jaguar program. |
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Keywords: | Diastereomeric isomerization Malachite green Hetaryl leuco-TAM molecules Carbinol form |
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