Highly fluorescent N,N-dimethylaminophenylethynylarenes: Synthesis, photophysical properties, and electrochemiluminescence

Journal of Physical Chemistry B

Volumn 109, Issue 18, 2005, Pages 8626-8633

  Ho, Tong Ing ^a   Elangovan, Arumugasamy ^a   Hsu, Hsien Yi ^a   Yang, Shu Wen ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMILUMINESCENCE; CHROMOPHORES; DENDRIMERS; ELECTRODES; ELECTROLUMINESCENCE; ELECTRONS; ENTHALPY; ORGANIC POLYMERS; SYNTHESIS (CHEMICAL);

ELECTROGENERATED CHEMILUMINESCENCE (ECL); ELECTRON TRANSFER PROCESSES; INTRAMOLECULAR COMMUNICATION; QUANTUM YIELDS;

AROMATIC COMPOUNDS;

EID: 19944384610     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0444518     Document Type: Article

References (71)

1. For reviews on NLO materials, see: (a) Nonlinear Optical Properties of Organic and Polymeric Materials; Williams, D. J., Ed.; ACS Symposium Series 233; American Chemical Society: Washington, DC, 1983.
2. (b) Nonlinear Optical Properties of Organic Molecules and Crystals; Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987; Vols. 1, 2.
3. (c) Organic Materials for Nonlinear Optics; Hahn, R. A., Ed.; Spec. Publ. No. 69; The Royal Society of Chemistry: London, 1989.
4. (d) Organic Materials for Nonlinear Optics II; Hahn R. A., Bloor, D., Eds.; Spec. Publ. No. 91; The Royal Society of Chemistry: Cambridge, U.K., 1991.
5. (e) Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: Chichester, U.K., 1991.
6. (f) Nalwa, H. S.; Miyata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1997.
7. (g) Lesley, M. J. G.; Woodward, A.; Taylor, N. J.; Marder, T. B.; Cazenobe, I.; Ledoux, I.; Zyss, J.; Thornton A.; Bruce D. W.; Kakkar A. K. Chem. Mater. 1998, 10, 1355.
8. For example, (a) Lee C.-H.; Yamamoto, T. Tetrahedron Lett. 2001, 42, 3993.
9. (b) Matsumi, N.; Naka K.; Chujo, Y. J. Am. Chem. Soc. 1998, 120, 5112.
10. (c) Wegner, G.; Müllen, K. Electronic Materials-the Oligomer Approach; Wiley-VCH: Weinheim, Germany, 1998.
11. (d) Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 1350.
12. (e) Odom, S. A.; Parkin, S. R.; Anthony, J. E. Org. Lett. 2003, 5, 4245.
13. For example, (a) Fang, J.-M.; Selvi, S.; Liao, J.-H. Slanina, Z.; Chen, C.-T.; Chou, P.-T. J. Am. Chem. Soc. 2004, 126, 3559.
14. (b) Inouye, M.; Takahashi K.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 341.
15. (a) Chen, C.-Y.; Ho, J.-H.; Wang, S.-L.; Ho, T.-I. Photochem. Photobiol. Sci. 2003, 2, 1232.
16. (b) Elangovan, A.; Chen, T.-Y.; Chen, C.-Y.; Ho, T.-I. Chem. Commun. 2003, 2146.
17. (c) Elangovan, A.; Yang, S.-W.; Lin, J.-H.; Kao, K.-M.; Ho, T.-I. Org. Biomol. Chem. 2004, 2, 1597.
18. (d) Elangovan, A.; Chiu, H.-H.; Yang, S.-W.; Ho, T.-I. Org. Biomol. Chem. 2004, 2, 3113.
19. (e) Elangovan, A.; Lin, J.-H.; Yang, S.-W.; Hsu, H.-Y.; Ho, T.-I. J. Org. Chem. 2004, 69, 8086.
20. (a) Makino, N.; Hoshi S.; Kitatani K. U.S. Patent 5093219, 1992.
21. (b) Zhan, X.; Liu, Y.; Yu, G.; Wu, X.; Zhu, D.; Sun, R.; Wang, D.; Epstein, A. J. J. Mater. Chem. 2001, 11, 1606.
22. (a) Suffert, J.; Ziessel, R. Tetrahedron Lett. 1991, 32, 757.
23. (b) Chanteau, S. H.; Tour, J. M.; Tetrahedron Lett. 2001, 42, 3057.
24. (c) Nakatsuji, S.; Matsuda, K.; Uesugi, Y.; Nakashima, K.; Akiyama S.; Fabian, W. J. Chem. Soc., Perkin Trans. 1 1992, 7, 755.
25. (d) Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science, 2001, 293, 1119.
26. (e) Percec, V.; Glodde, M.; Bera, T. K.; Miura, Y.; Shiyanovskaya, I.; Singer, K. D.; Balagurusamy, V. S. K.; Heiney, P. A.; Schnell, I.; Rapp, A.; Spiess, H.-W.; Hudson S. D.; Duan, H. Nature 2002, 419, 384.
27. (a) Holzapfel, M.; Lambert, C.; Selinka C.; Stalke, D. Chem. Soc., Perkin Trans. 2 2002, 2, 1553.
28. (b) Nelsen, S. F. Chem. Eur. J. 2000, 6, 581.
29. (c) Nelsen, S. F.; Adamus, J.; Wolff, J. J. J. Am. Chem. Soc. 1994, 116, 1589.
30. (d) Launay, J.-P. Chem. Soc. Rev. 2001, 30, 386.
31. (e) Lambert, C.; Nöll, G. J. Am. Chem. Soc. 1999, 121, 8434.
32. (f) Lambert, C.; Nöll, G. Angew. Chem., Int. Ed. 1998, 37, 2107.
33. (a) Onkelinx, A.; DeSchryver, F. C.; Viane, L.; Van der Auweraer, M.; Iwai, K.; Yamamoto, M.; Ichikawa, M.; Masuhara, H.; Maus M.; Rettig, W. J. Am. Chem. Soc. 1996, 118, 2892.
34. (b) Onkelinx, A.; Shweitzer, F.; De Schryver, F. C.; Miyasaki, H.; Van der Auweraer, M.; Asahi, T.; Masuhara, H.; Fukumura, H.; Yashima A.; Iwai, K. J. Phys. Chem. A 1997, 101, 5054.
35. (c) Maus, M.; Rettig, W.; Depaemelaere, S.; Onkelinx, A.; DeSchryver F. C.; Iwai. K. Chem. Phys. Lett. 1998, 292, 115.
36. (d) Kapturkiewicz, A.; Herbich, J.; Karpiuk, J.; Nowacki, J. J. Phys. Chem. A 1997, 101, 2332.
37. (e) Herbich J.; Kapturkiewicz, A. J. Am. Chem. Soc. 1998, 120, 1014 and references therein.
38. (a) Faulkner, L. R.; Bard, A. J. Electrogenerated Chemiluminescence; In Electrochemical methods; John Wiley & Sons: New York, 1980; pp 621-627.
39. (b) Oyama, M.; Okazaki, S. Anal. Chem. 1998, 70, 5079.
40. (c) Kapturkievicz, A. J. Electroanal. Chem. 1990, 290, 135.
41. (d) Kapturkievicz, A. J. Electroanal. Chem. 1991, 302, 13.
42. (e) Armstrong, N. R.; Whightman, R. M.; Gross, E. M. Annu. Rev. Phys. Chem. 2001, 52, 391.
43. (f) Richter, M. M. Chem. Rev. 2004, 104, 3003.
44. (g) Bard, A. J.; Faulkner, L. R. In Electroanalytical Chemistry; Bard, A. J., Ed.; Marcel-Dekker: New York, 1977; Vol. 10, p 3.
45. (a) Anderson, J. D.; McDonald, E. M.; Lee, P. A.; Anderson, M. L.; Ritchie, E. L.; Hall, H. K.; Hopkins, T.; Mash, E. A.; Wang, J.; Padias, A.; Thayumanavan, S.; Barlow, S.; Marder, S. R.; Jabbour, G. E.; Shaheen, S.; Kippelen, B.; Peyghambarian, N.; Wightman, R. M.; Armstrong, N. R. J. Am. Chem. Soc. 1998, 120, 9646.
46. (b) Armstrong, N. R.; Anderson, J. D.; Lee, P. A.; McDonald, E. M.; Wightman, R. M.; Hall, H. K.; Hopkins, T.; Padias, A.; Thayumanavan, S.; Barlow, S.; Marder, S. R. SPIE 1999, 3476, 178.
47. (c) Ketter, J. B.; Wightman, R. M. J. Am. Chem. Soc. 2004, 126, 10183.
48. Reynolds, G. A.; Drexhage, K. H. Opt. Commun. 1975, 13, 222.
49. Fery-Forgues, S.; Lavabre, D. J. Chem. Educ. 1999, 76, 1260.
50. (a) Elangovan, A.; Wang, Y.-H.; Ho, T.-I. Org. Lett. 2003, 5, 1841.
51. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
52. (a) Lakovickz, J. R. Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; p 187
53. (b) Lippert, Von E. Z. Elektrochem. 1957, 61, 962.
54. Watson, A. T.; Matsen, F. A. J. Chem. Phys. 1950, 18, 1305.
55. Faulkner, L. R.; Tachikawa, H.; Bard, A. J. J. Am. Chem. Soc. 1972, 94, 691.
56. (a) Morsi, S. E.; Carr, D.; El-Bayoumi, M. A. Chem. Phys. Lett. 1978, 58, 571.
57. (b) Ebeid, E. M.; El-Bayoumi, M. A.; Williams, J. O. J. Chem. Soc., Faraday Trans 1 1978, 74, 1457.
58. (c) Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure Appl. Chem. 1965, 11, 371.
59. (a) Visco, R. E.; Chandross, E. A. J. Am. Chem. Soc. 1964, 86, 5350.
60. (b) Chandross, E. A.; Longworth, J. W.; Visco, R. E. J. Am. Chem. Soc. 1965, 87, 3259.
61. (c) Faulkner, L. R.; Bard, A. J. J. Am. Chem. Soc. 1968, 90, 6284.
62. (d) Hercules, D. M. Science 1964, 145, 808.
63. McVey, J. K.; Shold, D. M.; Yang, N. C. J. Chem. Phys. 1976, 65, 3375.
64. int = 0.0226); final R indices [I > 2σ(I)]: R1 = 0.0451, wR2 = 0.1232; R indices (all data): R1 = 0.0582, wR2 = 0.1361.
65. (a) Birks, J. B. Photophysics of Aromatic Molecules; Wiley-Interscience: New York, 1970.
66. (b) Beens, H.; Weller, A. In Organic Molecular Photophysics; Birks, J. B., Ed.; John-Wiley & Sons: London, 1975; p 198.
67. All calculations were performed using Spartan '04 for Windows, Wavefunction Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612. (a) Hehre, W. J. A guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction Inc.: Irvine, CA, 2003.
68. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
69. Beck, A. D. J. Chem. Phys. 1993, 98, 5648.
70. (a) Handbook of Organic Solvents; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1995.
71. (b) Dean, J. A. Lange's handbook of chemistry, 14th ed.; McGraw-Hill: New York, 1992; pp 1.190, 5.104.