Bulletin of the Korean Chemical Society

  • 제30권11호
  • /
  • Pages.2608-2612
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  • 2009
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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X-ray Crystal Structure of Hetaryl Leuco-TAM Dyes, (2Z,2'E)-2,2'-(2-Phenyl Propane-1,3-diylidene) Bis(1,3,3-trimethyl indoline) Derivatives

  • Keum, Sam-Rok (Department of Advanced Material Chemistry, Korea University) ;
  • Roh, Se-Jung (Department of Advanced Material Chemistry, Korea University) ;
  • Kim, Young-Nan (Department of Advanced Material Chemistry, Korea University) ;
  • Im, Do-Hyuck (Department of Advanced Material Chemistry, Korea University) ;
  • Ma, So-Young (Department of Advanced Material Chemistry, Korea University)
  • 발행 : 2009.11.20
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초록

The unequivocal solid-state structure and stereochemistry of the hetaryl leuco-TAM dye, 2,2’-(2-phenyl propane- 1,3-diylidene) bis(1,3,3- trimethylindoline) derivatives were established using X-ray single crystal analysis. The X-ray crystal analysis showed that the (Z, E)-isomers only formed stereoselectively, with a so-called “threebladed propeller” conformation, from the reaction of a Fischer base and benzaldehyde derivatives. These isomers were stacked in a juxtaposition to form a dimer or a double dimer, adopting either a triclinic, with P-1, or monoclinic crystal system with a space group P21/n in the unit cell of the crystal.

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참고문헌

  1. Balko, L.; Allison, J. J. Foren. Sci. 2003, 48, 1172
  2. Kumar, D.; Singh, A. C.; Usha, P. N.; Tandon, R.; Triphathi, K. JAPI 2005, 53, 312
  3. Kher, A. A.; Green, E. V.; Mulholland, M. I. J. Foren. Sci. 2001, 46, 878
  4. Nair, V.; Thomas, S.; Mathew, S. C.; Abhilash, K. G. Tetrahedron 2006, 62, 6731 https://doi.org/10.1016/j.tet.2006.04.081
  5. Fabian, J.; Hartmann, H. In Light Absorption of Organic Colorants; Springer: Berlin-Heidelberg-New York, 1980
  6. Rys, P.; Zollinger, H. H. In Farbstoffchemie, Verlag Chemie; Weinheim: 1982
  7. Indig, G. L.; Anderson, G. S.; Nichols, M. G.; Bartlett, J. A.; Mellon, W. S.; Sieber, F. J. Pharm. Sci. 2000, 89, 88 https://doi.org/10.1002/(SICI)1520-6017(200001)89:1<88::AID-JPS9>3.0.CO;2-K
  8. Lurtz, M. M.; Pedersen, S. E. Mol. Pharmacol. 1999, 55, 159
  9. Cho, B. P.; Yang, T.; Lonnie, R.; Blankenship, L.; Moody, J. D.; Churchwell, M.; Beland, F. A.; Culp, S. J. Chem. Res. Toxicol. 2003, 19, 285
  10. Culp, S. J.; Beland, F. A.; Heflich, R. H.; Benson, R. W.; Blankenship, L. R.; Webb, P. J.; Mellick, P. W.; Trotter, R. W.; Shelton, S. D.; Greenlees, K. J.; Manjanatha, M. G. Mutation Res. 2002, 506, 55
  11. Keum, S. R.; Roh, S. J.; Lee, M. H.; Saurial, F.; Buncel, E. Magn. Reson. Chem. 2008, 46, 872 https://doi.org/10.1002/mrc.2255
  12. SMART & SANIT software reference manuals, version 4.0; Siemens Energy and Automation, Inc. Analytical Instrumentation; Madison, Wisconsin, USA, 1996
  13. SHELXTL reference manual, Version 5.03; Siemens Energy & Automation, Inc., Analytical Instrumentation; Madison, Wisconsin, USA, 1996
  14. Mislow, K. Acc. Chem. Res. 1976, 9, 26 https://doi.org/10.1021/ar50097a005
  15. Pindur, U. J. Heter. Chem. 1982, 19, 1371 https://doi.org/10.1002/jhet.5570190622
  16. Edgar, W.; Garbisch, E. W. J. Am. Chem. Soc. 1964, 86, 5561 https://doi.org/10.1021/ja01078a032
  17. Miller, B. In Advanced Organic Chemistry: Reactions and Mechanisms, $2^n^d$ Ed.; Pearson Education International: 2004; Chapter 1, p 17
  18. Tarbin, J. A.; Barnes, K. A.; Bygrave, J.; Farrington, W. H. Anal. 1998, 123, 2567 https://doi.org/10.1039/a805200j
  19. Le Goff, T.; Wood, S. Anal. Bioanal. Chem. 2008, 391, 2035 https://doi.org/10.1007/s00216-008-2048-2

피인용 문헌

  1. Unusual Stability of Diastereomers of the Isomeric Pyridine-based Leuco-TAM Dyes 2,2'-(2-(Pyridin-4 or 3-yl)propane-1,3-diylidene)bis(5-chloro-1,3,3-trimethylindoline) vol.33, pp.2, 2012, https://doi.org/10.5012/bkcs.2012.33.2.681
  2. Unsymmetrically Substituted Leuco-Triarylmethane Molecules Formed from the Reaction of a Fischer's Base and α,β-Unsaturated Iminium Salts via a Michael-Type Reaction vol.34, pp.5, 2013, https://doi.org/10.5012/bkcs.2013.34.5.1563
  3. Novel dimeric leuco-TAM dyes, 1,4-bis{(1E,3Z)-1,3-bis(1,3,3-trimethylindolin-2-ylidene)propan-2-yl}benzene derivatives: Structure and spectroscopic characterization vol.1014, pp.None, 2009, https://doi.org/10.1016/j.molstruc.2012.02.002