Design, synthesis, and structural and spectroscopic studies of push-pull two-photon absorbing chromophores with acceptor groups of varying strength

Journal of Organic Chemistry

Volumn 78, Issue 3, 2013, Pages 1014-1025

  Morales, Alma R ^a   Frazer, Andrew ^a   Woodward, Adam W ^a   Ahn White, Hyo Yang ^a   Fonari, Alexandr ^b   Tongwa, Paul ^b   Timofeeva, Tatiana ^b   Belfield, Kevin D ^a  

^a UNIVERSITY OF CENTRAL FLORIDA   (United States)

^b NEW MEXICO HIGHLANDS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACCEPTOR GROUPS; ELECTRON ACCEPTOR; ELECTRON-ACCEPTING; ELECTRON-DONATING; GENERAL TRENDS; GEOMETRICAL PROPERTY; MALONONITRILES; MOLECULAR SYMMETRY; NONLINEAR SPECTROSCOPIC TECHNIQUES; OPTICAL NONLINEARITY; QUANTUM CHEMICAL CALCULATIONS; SINGLE CRYSTAL X-RAY DIFFRACTION; SPECTROSCOPIC STUDIES; TWO PHOTON; TWO PHOTON ABSORPTION (2PA);

CHARGE TRANSFER; CHEMICAL COMPOUNDS; LIGHT ABSORPTION; NONLINEAR OPTICS; QUANTUM CHEMISTRY; SPECTROSCOPIC ANALYSIS; STRUCTURAL DESIGN; TWO PHOTON PROCESSES; X RAY DIFFRACTION;

CHROMOPHORES;

FLUORENE DERIVATIVE; MALONONITRILE;

ARTICLE; CALCULATION; CHEMICAL STRUCTURE; CHROMATOPHORE; ELECTRIC POTENTIAL; ELECTRON; PHOTON ABSORPTIOMETRY; SPECTROSCOPY; SYNTHESIS; TENSILE STRENGTH; X RAY DIFFRACTION;

ABSORPTION; CRYSTALLOGRAPHY, X-RAY; NITRILES; PHOTONS; PYRANS; QUANTUM THEORY; SPECTROMETRY, FLUORESCENCE; X-RAY DIFFRACTION;

EID: 84873369133     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302423p     Document Type: Article

References (54)

1. Göppert-Mayer, M. Ann. Phys. 1931, 9, 273-295
2. He, G. S.; Markowicz, P. P.; Lin, T.-C.; Prasad, P. N. Nature 2002, 415, 767-770
3. Blanchard-Desce, M. C. R. Phys. 2002, 3, 439-448
4. Belfield, K. D.; Schafer, K. J.; Liu, Y.; Liu, J.; Ren, X.; Van Stryland, E. W. J. Phys. Org. Chem. 2000, 13, 837-849
5. Denk, W.; Strickler, J. H.; Webb, W. W. Science 1990, 248, 73-76
6. Shen, Y.; Jakubczyk, D.; Xu, F.; Swiatkiewicz, J.; Prasad, P. N.; Reinhardt, B. A. Appl. Phys. Lett. 2000, 76, 1-3
7. Xu, C.; Williams, R. M.; Zipfel, W.; Webb, W. W. Bioimaging 1996, 4, 198-207
8. Reinhardt, B. A.; Brott, L. L.; Clarson, S. J.; Dillard, A. G.; Bhatt, J. C.; Kannan, R.; Yuan, L.; He, G. S.; Prasad, P. N. Chem. Mater. 1998, 10, 1863-1874
9. Baur, J. W.; Alexander, M. D.; Banach, M., Jr.; Denny, L. R.; Reinhardt, B. A.; Vaia, R. A.; Fleitz, P. A.; Kirkpatrick, S. M. Chem. Mater. 1999, 11, 2899-2906
10. Lee, K.-S.; Lee, J.-H.; Kim, K.-S.; Woo, H.-Y.; Kim, O.-K.; Choi, H.; Cha, M.; He, G. S.; Swiatkiewcz, J.; Prasad, P. N.; Chung, M.- A.; Jung, S.-D. MCLC S&T, Sect. B: Nonlinear Opt. 2001, 27, 133-137
11. Morel, Y.; Irimia, A.; Najechalski, Y.; Kervella, Y.; Stephan, O.; Baldeck, P. L.; Andraud, C. J. Chem. Phys. 2001, 114, 5391-5396
12. Charlot, M.; Izard, N.; Mongin, O.; Riehl, D.; Blanchard-Desce, M. Chem. Phys. Lett. 2006, 417, 297-302
13. Reinhardt, B. A. Photonics Sci. News 1999, 4, 21-34
14. Prasad, P. N.; Bhawalkar, J. D.; Kumar, N. D.; Lal, M. Macromol. Symp. 1997, 118, 467-472
15. Bhawalkar, J. D.; Kumar, N. D.; Zhao, C. F.; Prasad, P. N. J. Clin. Laser Med. Surg. 1997, 15, 201-204
16. Verbiest, T.; Houbrechts, S.; Kauranen, M.; Clays, K.; Persoons, A. J. Mater. Chem. 1997, 7, 2175-2189
17. Le Bozec, H.; Renouard, T. Eur. J. Inorg. Chem. 2000, 2000, 229-239
18. Wolf, J. J.; Wortmann, R. Adv. Phys. Org. Chem. 1999, 32, 121-217
19. Long, N. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 21-38
20. Steybe, F.; Effenberger, F.; Gubler, U.; Bosshard, C.; Günter, P. Tetrahedron 1998, 54, 8469-8480
21. Albota, M.; Beljonne, D.; Bredas, J.-L.; Ehrlich, J. E.; Fu, J.-Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.; McCord- Maughon, D.; Perry, J. W.; Rockel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X.-L.; Xu, C. Science 1998, 281, 1653-1656
22. Marder, S. R.; Gorman, C. B.; Meyers, F.; Perry, J. W.; Bourhill, G.; Bredas, J. L.; Pierce, B. M. Science 1994, 265, 632-635
23. Oudar, J. L. J. Chem. Phys. 1977, 67, 446-457
24. Strehmel, B.; Sarker, A. M.; Detert, H. Chem. Phys. Chem. 2003, 4, 249-259
25. Mignani, G.; Leising, F.; Meyruex, R.; Samson, H. Tetrahedron Lett. 1990, 31, 4743-4746
26. Jen, A. K.-Y.; Rao, V. P.; Drost, K. J.; Wong, K. Y.; Cava, M. P. J. Chem. Soc., Chem. Commun. 1994, 2057-2058
27. Rao, V. P.; Cai, Y. M.; Jen, A. K.-Y. J. Chem. Soc., Chem. Commun. 1994, 14, 1689-1690
28. Wu, X.; Wu, J.; Liu, Y.; Jen, A.K.-Y. J. Am. Chem. Soc. 1999, 121, 472-473
29. Belfield, K. D.; Bondar, M. V.; Przhonska, O. V.; Schafer, K. J. J. Fluoresc. 2002, 12, 449-454
30. Belfield, K. D.; Schafer, K. J.; Mourad, W.; Reinhardt, B. A. J. Org. Chem. 2000, 65, 4475-4481
31. Belfield, K. D.; Morales, A. R.; Hales, J. M.; Hagan, D. J.; Van Stryland, E. W.; Chapela, V. M.; Percino J. Chem. Mater. 2004, 16, 2267-2273
32. Belfield, K. D.; Morales, A. R.; Kang, B.-S.; Hales, J. M.; Hagan, D. J.; Van Stryland, E. W.; Chapela, V. M.; Percino J. Chem. Mater. 2004, 16, 4634-4641
33. Morales, A. R.; Belfield, K. D.; Hales, J. M.; Van Stryland, E. W.; Hagan, D. J. Chem. Mater. 2006, 18, 4972-4980
34. Yao, S.; Belfield, K. D. J. Org. Chem. 2005, 70, 5126-5132
35. Chiang, C.-L.; Wu, M.-F.; Dai, D.-C.; Wen, Y.-S.; Wang, J.-K.; Chen, C.-T. Adv. Funct. Mater. 2005, 15, 231-238
36. Bello, K. A.; Cheng, L.; Griffiths, J. J. Chem. Soc., Perkin Trans 2 1987, 6, 815-818
37. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Kluwer Academic/Plenum: New York, 1999; Vol. 648, pp 52-53, 298-300.
38. Rebane, A.; Drobizhev, M.; Makarov, N. S.; Beuerman, E.; Haley, J. E.; Krein, D. M.; Burke, A. R.; Flikkema, J. L.; Cooper, T. M. J. Chem. Phys. A 2011, 115, 4255-4262
39. http://spie.org/x648.html?product-id=796745.
40. Kannan, R.; He, G. S.; Yuan, L.; Xu., F.; Prasad, P. N.; Dombroskie, A. G.; Reinhardt, B. A.; Baur, J. W.; Vaia, R. A.; Tan, L.-S. Chem. Mater. 2001, 13, 1896-1904
41. Sheik-Bahae, M.; Said, A. A.; Wei, T. H.; Hagan, D. J.; Van Stryland, E. W. IEEE J. Quantum Elect. 1990, 26, 760-769
42. Xu, C.; Webb, W. W. J. Opt. Soc. Am. B 1996, 13, 481-491
43. Makarov, N. S.; Drobizhev, M.; Rebane, A. Opt. Express 2008, 16, 4029-4047
44. Fu, J.; Padilha, L. A.; Hagan, D. J.; Van Stryland, E. W.; Przhonska, O. V.; Bondar, M. V.; Slominsky, Y. L.; Kachkovski, A. D. J. Opt. Soc. Am. B 2007, 24, 67-76
45. Padilha, L. A.; Webster, S.; Przhonska, O. V.; Hu, H. H.; Peceli, D.; Rosch, J. L.; Bondar, M. V.; Gerasov, A. O.; Kovtun, Y. P.; Shandura, M. P.; Kachkovski, A. D.; Hagan, D. J.; Van Stryland, E. W. J. Mater. Chem. 2009, 19, 7503-7513
46. SAINT+, Version 6.2a; Bruker Analytical X-ray System, Inc., Madison, WI, 2001.
47. SADABS; Bruker Analytical X-ray System, Inc., Madison, WI, 1999.
48. SHELXTL, Version 6.10; Bruker Analytical X-ray System, Inc., Madison, WI, 1997.
49. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, M.; Hada, M.; Ehara, K.; Toyota, R.; Fukuda, J.; Hasegawa, M.; Ishida, T.; Nakajima; Honda, J. L. Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc., Wallingford, CT, 2009.
50. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
51. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B. 1988, 37, 785-789
52. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211
53. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
54. Martin, R. L. J. Chem. Phys. 2003, 118, 4775-4777