Anomalous photophysics of bis(hydroxystyryl)benzenes: A twist on the para/meta dichotomy

Organic Letters

Volumn 10, Issue 12, 2008, Pages 2429-2432

  Solntsev, Kyril M ^a   McGrier, Psaras L ^a   Fahrni, Christoph J ^a   Tolbert, Laren M ^a   Bunz, Uwe H F ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; PHOTOCHEMISTRY; SPECTROFLUOROMETRY; STEREOISOMERISM; SYNTHESIS;

BENZENE DERIVATIVES; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM;

EID: 48849085633     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8006925     Document Type: Article

References (29)

1. Benfaremo, N.; Sandman, D. J.; Tripathy, S.; Kumar, J.; Yang, K.; Rubner, M. F.; Lyons, C. Macromolecules 1998, 31, 3595-3599.
2. For leading references, see: (a) Saltiel, J.; Sun, Y. P. J. Phys. Chem. 1989, 93, 6246-50.
3. (b) Meier, H. Angew. Chem., Int. Ed. 1992, 31, 1399-1440.
4. (c) Waldeck, D. H. J. Mol. Liq. 1993, 57, 127-148.
5. Sandros, K.; Sundahl, M.; Wennerström, O.; Norinder, U. J. Am. Chem. Soc. 1990, 112, 3082-3086.
6. Fengqiang, Z.; Motoyoshiya, J.; Nakamura, J.; Nishii, Y.; Aoyama, H. Photochem. Photobiol. 2006, 82, 1645-1650.
7. (a) Lewis, F. D.; Crompton, E. M. J. Am. Chem. Soc. 2003, 125, 4044-4045.
8. (b) Crompton, E. M.; Lewis, F. D. Photochem. Photobiol. Sci. 2004, 3, 660-668.
9. (c) Lewis, F. D.; Sinks, L. E.; Weigel, W.; Sajimon, M. C.; Crompton, E. M. J. Phys. Chem. A 2005, 109, 2443-2451.
10. Canals, I.; Oumada, F. Z.; Roses, M.; Bosch, E. J. Chromatogr. A 2001, 911, 191-202.
11. Binstead, R. A.; Zuberbühler, A. D.; Jung, B. SPECFIT V. 3.0.40; Spectrum Software Associates: Marlborough, MA, 2007.
12. Grabowski, Z. R.; Grabowska, A. Z. Phys. Chem. N.F. 1976, 101, 197-208.
13. Tolbert, L. M.; Solntsev, K. M. Acc. Chem. Res. 2002, 35, 19-27.
14. Solntsev, K. M.; Poizat, P.; Dong, J.; Rehault, J.; Lou, Y.; Burda, C.; Tolbert, L. M. J. Phys. Chem. B 2008, 112, 2700-2711.
15. Hsu, F.-C.; Hayashi, M.; Wang, H.-W.; Lin, S. H.; Wang, J.-K. J. Phys. Chem. 2007, 111, 759-763.
16. (a) Borden, W. T.; Davidson, E. R. J. Am. Chem. Soc. 1977, 99, 4587-4594.
17. (b) Properly speaking, "disjoint" refers to diradicals, but the description applies to radical anions and dianions as well.
18. (a) Wilson, J. N.; Bunz, U. H. F. J. Am. Chem. Soc. 2005, 127, 4124-4125.
19. (b) Zucchero, A. J.; Wilson, J. N.; Bunz, U. H. F. J. Am. Chem. Soc. 2006, 128, 11872-11881.
20. (a) Lower, S. K.; El-Sayed, M. A. Chem. Rev. 1966, 66, 199-241.
21. (b) El-Sayed, M. A. Acc. Chem. Res. 1968, 1, 8-16.
22. (a) Brederek, K.; Forster, T.; Oesterlin, H. G. Luminescence of Organic and Inorganic Materials; Kallman, H. P., Sprunch, G. M.; Eds.; Wiley: New York, 1962; p. 161.
23. (b) Young, V, Jr.; Quiring, H. L.; Sykes, A. G. J. Am. Chem. Soc. 1997, 119, 12477-12480.
24. (c) Leray, I.; Lefevre, J. P.; Delouis, J. F.; Delaire, J.; Valeur, B. Chem. - Eur. J. 2001, 7, 4590-4598.
25. (d) Zhou, Z.; Fahrni, C. J. J. Am. Chem. Soc. 2004, 126, 8862-8863.
26. Head-Gordon, M.; Grana, A. M.; Maurice, D.; White, C. A. J. Phys. Chem. 1995, 99, 14261-14270.
27. IUPAC names: 4,4′-(1E,1′E)-2,2′-(2,5- bis((4-tert-butylphenyl)ethynyl)-1,4-phenylene)bis(ethene-2,1-diyl) diphenol and 3,3′-(1E,1′E)-2,2′-(2,5-bis((4- tert-butylphenyl)ethynyl)-1,4-phenylene)bis(ethene-2,1-diyl)diphenol.
28. McGrier, P. L.; Solntsev, K. M.; Schönhaber, J.; Brombosz, S. M.; Tolbert, L. M.; Bunz, U. H. F. Chem. Commun. 2007, 2127-2129.
29. Hudson, B.; Kohler, B. Synth. Met. 1984, 9, 241-53.