Unsymmetric leuco-TAM dyes, (2E, 2 ' E)-2,2 '-{(E)-4-phenylpent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives. Part II: X-ray crystal structure
- Authors
- Keum, Sam-Rok; Ma, So-Young; Kim, Do-Kyung; Lim, Hyun-Woo; Roh, Se-Jung
- Issue Date
- 9월-2012
- Publisher
- ELSEVIER SCI LTD
- Keywords
- Unsymmetrical leuco-TAM; Unsymmetric three-bladed propeller conformation; EEE isomers; Stereoselective formation; Near-IR dyes; Cy5 TAM(+) dye
- Citation
- DYES AND PIGMENTS, v.94, no.3, pp.490 - 495
- Indexed
- SCIE
SCOPUS
- Journal Title
- DYES AND PIGMENTS
- Volume
- 94
- Number
- 3
- Start Page
- 490
- End Page
- 495
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/107528
- DOI
- 10.1016/j.dyepig.2012.02.007
- ISSN
- 0143-7208
- Abstract
- The unequivocal solid-state structure and stereochemistry of the unsymmetric leuco-triarylmethane (Un-LTAM) dye 2,2'-{(E)-4-(phenyl)pent-2-ene-1,5-diylidene}bis(1,3,3-trimethylindoline) derivatives were established using X-ray single-crystal analysis. The X-ray analysis showed that the EEE isomers were formed stereoselectively with an unsymmetric three-bladed propeller conformation from the reaction of a Fischer's base and cinnamaldehyde derivatives. The 5,5'-dichloro-4 ''-nitro-triarylmethane dye displayed a triclinic crystal structure with the space group P-1. The molecules stack alternately to form a dimer, adopting intermolecular distances of 8.53 and 9.40 angstrom for rings B and C, respectively. Unsymmetric triarylmethane cations, the oxidized form of these dyes, have UV absorptions over 680 nm and selected examples absorb close to the near-IR region. (C) 2012 Elsevier Ltd. All rights reserved.
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