Synthesis and Optical Properties of Donor-Acceptor Tetrakis(phenyl-ethynyl) benzenes

Synlett

Volumn , Issue 1, 2004, Pages 165-168

  Miller, Jeremie J ^a   Marsden, Jeremiah A ^a   Haley, Michael M ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

Alkynes; Arenes; Chromophores; Cross coupling; Palladium

Indexed keywords

BENZENE DERIVATIVE; PHENYL GROUP;

ARTICLE; CHELATION; CHEMICAL BOND; MATERIALS; MOLECULE; OPTICS; PHYSICAL CHEMISTRY; POLARIZATION; SYNTHESIS; TEMPERATURE;

EID: 0347601758     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43372     Document Type: Article

References (30)

1. (a) Pak, J. J.; Brand, S. C.; Haley, M. M. Top. Curr. Chem. 1999, 201, 81.
2. (b) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605.
3. (c) Young, J. K.; Moore, J. S. In Modern Acetylene Chemistry; Stang, P. J.; Diederich, F., Eds.; VCH: Weinheim, 1995, 415-442.
4. (2) Inter alia: (a) Conjugated Polymers and Related Materials: The Interconnection of Chemical and Electronic Structure; Saleneck, W. R.; Lundström, I.; Ranby, B., Eds.; Oxford University Press: Oxford, UK, 1993. (b) Photonic and Optoelectronic Polymers; Jenekhe, S. A.; Wynne, K. J., Eds.; American Chemical Society: Washington, DC, 1995. (c) Electronic Materials: The Oligomer Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998. (d) Tour, J. M. Chem. Rev. 1998, 96, 537. (e) Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863.
5. Inter alia: (a) Conjugated Polymers and Related Materials: The Interconnection of Chemical and Electronic Structure; Saleneck, W. R.; Lundström, I.; Ranby, B., Eds.; Oxford University Press: Oxford, UK, 1993. (b) Photonic and Optoelectronic Polymers; Jenekhe, S. A.; Wynne, K. J., Eds.; American Chemical Society: Washington, DC, 1995. (c) Electronic Materials: The Oligomer Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998. (d) Tour, J. M. Chem. Rev. 1998, 96, 537. (e) Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863.
6. Inter alia: (a) Conjugated Polymers and Related Materials: The Interconnection of Chemical and Electronic Structure; Saleneck, W. R.; Lundström, I.; Ranby, B., Eds.; Oxford University Press: Oxford, UK, 1993. (b) Photonic and Optoelectronic Polymers; Jenekhe, S. A.; Wynne, K. J., Eds.; American Chemical Society: Washington, DC, 1995. (c) Electronic Materials: The Oligomer Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998. (d) Tour, J. M. Chem. Rev. 1998, 96, 537. (e) Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863.
7. Inter alia: (a) Conjugated Polymers and Related Materials: The Interconnection of Chemical and Electronic Structure; Saleneck, W. R.; Lundström, I.; Ranby, B., Eds.; Oxford University Press: Oxford, UK, 1993. (b) Photonic and Optoelectronic Polymers; Jenekhe, S. A.; Wynne, K. J., Eds.; American Chemical Society: Washington, DC, 1995. (c) Electronic Materials: The Oligomer Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998. (d) Tour, J. M. Chem. Rev. 1998, 96, 537. (e) Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863.
8. Inter alia: (a) Conjugated Polymers and Related Materials: The Interconnection of Chemical and Electronic Structure; Saleneck, W. R.; Lundström, I.; Ranby, B., Eds.; Oxford University Press: Oxford, UK, 1993. (b) Photonic and Optoelectronic Polymers; Jenekhe, S. A.; Wynne, K. J., Eds.; American Chemical Society: Washington, DC, 1995. (c) Electronic Materials: The Oligomer Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998. (d) Tour, J. M. Chem. Rev. 1998, 96, 537. (e) Schwab, P. F. H.; Levin, M. D.; Michl, J. Chem. Rev. 1999, 99, 1863.
9. Marsden, J. A.; Palmer, J. G.; Haley, M. M. Eur. J. Org. Chem. 2003, 2355.
10. (a) Pak, J. J.; Weakley, T. J. R.; Haley, M. M. J. Am. Chem. Soc. 1999, 121, 8182.
11. (b) Sarkar, A.; Pak, J. J.; Rayfield, G. W.; Haley, M. M. J. Mater. Chem. 2001, 11, 2943.
12. Marsden, J. A.; Miller, J. J.; Haley, M. M., manuscript in preparation.
13. Kondo, K.; Yasuda, S.; Sakaguchi, T.; Miya, M. Chem. Commun. 1995, 55-56.
14. Du, C.-J. F.; Hart, H. J. Org. Chem. 1987, 4311.
15. (a) Venkataraman, D.; Gardner, G. B.; Lee, S.; Moore, J. S. J. Am. Chem. Soc. 1995, 117, 11600.
16. (b) Gardner, G. B.; Kiang, Y.-H.; Lee, S.; Asgaonkar, A.; Venkataraman, D. J. Am. Chem. Soc. 1996, 118, 6946.
17. (c) Kiang, Y.-H.; Gardner, G. B.; Lee, S.; Xu, Z.; Lobkovsky, E. B. J. Am. Chem. Soc. 1999, 121, 8204.
18. (a) Swager, T. M. Acc. Chem. Res. 1998, 31, 201.
19. (b) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1073.
20. (c) Yamamoto, T. Bull. Chem. Soc. Jpn. 1999, 72, 621.
21. 3): δ = 13.98, 20.30, 29.32, 50.65, 85.76, 92.55, 93.35, 98.87, 107.77, 111.14, 122.06, 123.64, 127.85, 130.18, 132.25, 133.12, 134.00, 135.20, 146.93, 148.50.
22. 3): δ = 11.32, 13.98, 18.77, 20.31, 29.36, 50.66, 85.97, 96.06, 97.11, 104.98, 108.56, 111.14, 123.76, 125.72, 133.16, 135.95, 148.17.
23. (a) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Stang, P. J.; Diederich, F., Eds.; VCH: Weinheim, 1997, 203-229.
24. (b) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979.
25. Miljanic, O. S.; Vollhardt, K. P. C.; Whitener, G. D. Synlett 2003, 29.
26. Thorand, S.; Krause, W. J. Org. Chem. 1998, 63, 8551.
27. Slepkov, A. D.; Hegmann, F. A.; Marsden, J. A.; Miller, J. J.; Haley, M. M.; Tykwinski, R. R., work in progress.
28. (a) Reinhardt, B. A.; Brott, L. L.; Clarson, S. J.; Dillard, A. G.; Bhatt, J. C.; Kannan, R.; Yuan, L. X.; He, G. S.; Prasad, P. N. Chem. Mater. 1998, 10, 1863.
29. (b) Kim, O. K.; Lee, K. S.; Woo, H. Y.; Kim, K. S.; He, G. S.; Swiatkiewicz, J.; Prasad, P. N. Chem. Mater. 2000, 12, 284.
30. (c) For measurement techniques: Slepkov, A. D.; Hegmann, F. A.; Zhao, Y. M.; Tykwinski, R. R.; Kamada, K. J. Chem. Phys. 2002, 116, 3834.