Exciton chirality in trans-1,2-diamidocyclohexanes: Fluorescent chromophores

Chirality

Volumn 17, Issue 6, 2005, Pages 316-322

  Boiadjiev, Stefan E ^a   Lightner, David A ^a  

^a UNIVERSITY OF NEVADA   (United States)

Author keywords

Circular dichroism; Diamines; Dipyrrinones

Indexed keywords

1,2 DIAMIDOCYCLOHEXANE DERIVATIVE; BENZOIC ACID; CYCLOHEXANE DERIVATIVE; DIAMIDE; ORGANIC SOLVENT; PROPIONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; FLUORESCENCE; LIGHT ABSORPTION; PRIORITY JOURNAL; QUANTUM YIELD; STEREOCHEMISTRY; SYNTHESIS;

BRIDGED COMPOUNDS; CIRCULAR DICHROISM; CYCLOHEXANES; FLUORESCENT DYES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY; STEREOISOMERISM;

EID: 21844474262     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20170     Document Type: Article

References (22)

1. Falk H. The chemistry of linear oligopyrroles and bile pigments. Wien: Springer-Verlag; 1989.
2. Falk H, Vormayr G, Margulies L, Metz S, Mazur Y. A linear dichroism study of pyrromethene-, pyrromethenone-, and bilatriene-abc derivatives. Monatsh Chem 1986;117:849-858.
3. (a) Byun YS, Lightner DA. Exciton coupling from dipyrrinone chromophores. J Org Chem 1991;56:6027-6033.
4. (b) Byun YS, Lightner DA. Long-range exciton coupling from dipyrrinone chromophores. Tetrahedron 1991;47:9759-9772.
5. Brower JO, Lightner DA. Synthesis and spectroscopic properties of a new class of highly fluorescent dipyrrinones. J Org Chem 2002;67: 2713-2717.
6. Lightner DA, Gawroński JK, Wijekoon WMD. Complementarity and chiral recognition: enantioselective complexation of bilirubin. J Am Chem Soc 1987;109:6354-6362.
7. Falk H, Grubmayr K, Höllbacher G, Hofer O, Leodolter A, Neufingerl F, Ribó JM. Pyrromethenone-Partialstrukturen von Gallenpigmenten: Struktur und Eigenschaften in Lösung. Monatsh Chem 1977;108: 1113-1130.
8. Kawai M, Nagai U, Katsumi M. CD-spectra of N,N′-dibenzoylamino acids and related compounds. Evidence for the conformation of acyclic diamino compounds. Tetrahedron Lett 1975;3165-3166.
9. Harada N, Nakanishi K. Circular dichroic spectroscopy-exciton coupling in organic stereochemistry. Mill Valley, CA: University Science Books; 1983. 156 p.
10. Gawroński J, Kolbon H, Kwit M. The use of benzamide derivatives of secondary amines for stereochemical studies by circular dichroism. Enantiomer 2002;7:85-92.
11. Whitener GD, Hagadorn JR, Arnold J. Synthesis and characterization of a new class of chelating bis(amidinate) ligands. J Chem Soc Dalton Trans 1999;1249-1255.
12. 2υ symmetrical 2,3-haphthalenedicarboximido chromophore. Enantiomer 1998;3: 197-202.
13. Gargiulo D, Ikemoto N, Odingo J, Bozhkova N, Iwashita T, Berova N, Nakanishi K. CD exciton chirality method: Schiff base and cyanine dye-type chromophores for primary amine groups. J Am Chem Soc 1994;116:3670-3677.
14. Tanaka K, Pescitelli G, Nakanishi K, Berova N. Fluorescence detected exciton coupled circular dichroism: development of new fluorescent separator groups for structural studies. Monatsh Chem 2005;136: 367-395.
15. Nehira T. Fluorescence detected circular dichroism for highly sensitive observation of exciton coupled CD. Monatsh Chem 2005;136: 477-487.
16. Boiadjiev SE, Lightner DA. Intensely fluorescent dipyrrinones. J Phys Org Chem 2004;17:675-679.
17. Boiadjiev SE, Lightner DA. Novel benzoic acid congeners of bilirubin. J Org Chem 2003;68:7591-7604.
18. Boiadjiev SE, Lightner DA. Exciton chirality: (A) origin and (B) application from strongly fluorescent dipyrrinone chromophores. Monatsh Chem 2005;136:489-508.
19. Boiadjiev SE, Lightner DA. Conformational control by remote chiral centers. Linear tetrapyrroles. Tetrahedron: Asymmetry 2004;15: 3301-3305.
20. Boiadjiev SE, Lightner DA. Strongly fluorescent dipyrrinones-substituent effects. J Heterocycl Chem 2004;41:1033-1037.
21. PC MODEL, ver. 8.5, using the MMX force field. Bloomington, IN: Serena Software (http://www.serenasoft.com).
22. Eaton DF. Luminescence spectroscopy. In: Scaiano JC, editor. Handbook of organic photochemistry. Boca Raton, FL: CRC Press; 1989. Vol 1, p 231-239.