Two-photon absorption in cross-shaped chromophores with phenylene-vinylene backbones

Proceedings of SPIE - The International Society for Optical Engineering

Volumn 6891, Issue , 2008, Pages

  Rumi, Mariacristina ^a   Pond, Stephanie J K ^b   Zhang, Qing ^a,b   Bishop, Maximilienne ^b   Zhang, Yadong ^b   Barlow, Stephen ^a,b   Marder, Seth R ^a   Perry, Joseph W ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b University of Arizona   (United States)

Author keywords

Molecular exciton; Multi branched chromophores; Quadrupolar chromophores; Two photon absorption

Indexed keywords

(DIACETOXYIODO) BENZENE; (PL) PROPERTIES; ADDITIVITY; AROMATIC CORES; CONJUGATED BACKBONES; COUPLING INTERACTIONS; CROSS SECTIONING; GENERAL (CO); MONOMER UNITS; MULTI DIMENSIONAL; ONE-DIMENSION; ORGANIC MOLECULES; PHOTONIC MATERIALS; PYRAZINE (A); RELATIVE ORIENTATION; RESEARCH EFFORTS; STRENGTH (IGC: D5/D6); TPA CROSS SECTIONS; TWO PHOTON SPECTRA; TWO-PHOTON-ABSORPTION (TPA);

ABSORPTION; ARCHITECTURAL DESIGN; AROMATIC COMPOUNDS; BENZENE; CHROMOPHORES; LEAD; LUMINESCENCE OF ORGANIC SOLIDS; MIXTURES; MOLECULAR STRUCTURE; MOLECULES; MONOMERS; MULTIPHOTON PROCESSES; NANOSTRUCTURED MATERIALS; OPTICAL MATERIALS; ORGANIC POLYMERS; PHOTONS; PIGMENTS; STRUCTURAL DESIGN; TELLURIUM COMPOUNDS;

LIGHT ABSORPTION;

EID: 42149183522     PISSN: 0277786X     EISSN: None     Source Type: Conference Proceeding    
DOI: 10.1117/12.761818     Document Type: Conference Paper

References (43)

1. J. H. Strickler, and W. W. Webb, "Two-photon excitation in laser scanning fluorescence microscopy," Proc. SPIE 1398, 107-118 (1990).
2. S. Maruo, O. Nakamura, and S. Kawata, "Three-dimensional microfabrication with two-photon-absorbed photopolymerization," Opt. Lett. 22, 132-134 (1997).
3. B. H. Cumpston, S. P. Ananthavel, S. Barlow, D. L. Dyer, J. E. Ehrlich, L. L. Erskine, A. A. Heikal, S. M. Kuebler, I.-Y. S. Lee, D. McCord-Maughon, J. Qin, H. Röckel, M. Rumi, X.-L. Wu, S. R. Marder, and J. W. Perry, "Two-photon polymerization initiators for three-dimensional optical data storage and microfabrication," Nature 398, 51-54 (1999).
4. W. Denk, J. H. Strickler, and W. W. Webb, "Two-photon laser scanning fluorescence microscopy," Science 248, 73-76(1990).
5. W. Denk, D. W. Piston, and W. W. Webb, In Handbook of Biological Confocal Microscopy; Pawley, J. B., Ed.; Plenum Press, New York, 1995, pp 445-45d.
6. S. W. Hell, S. Lindek, and E. H. K. Stelzer, "Enhancing the axial resolution in far-field light microscopy: two-photon 4Pi confocal fluorescence microscopy," J. Mod. Opt. 41, 675-681 (1994).
7. G. S. He, G. C. Xu, P. N. Prasad, B. A. Reinhardt, J. C. Bhatt, and A. G. Dillard, "Two-photon absorption and optical-limiting properties of novel organic compounds," Opt. Lett. 20, 435-437 (1995).
8. J. E. Ehrlich, X. L. Wu, I.-Y. S. Lee, Z.-Y. Hu, H. Röckel, S. R. Marder, and J. W. Perry, "Two-photon absorption and broadband optical limiting with bis-donor stilbenes," Opt. Lett. 22, 1843-1845 (1997).
9. M. Albota, D. Beljonne, J.-L. Brédas, J. E. Ehrlich, J.-Y. Fu, A. A. Heikal, S. E. Hess, T. Kogej, M. D. Levin, S. R. Marder, D. McCord-Maughon, J. W. Perry, H. Röckel, M. Rumi, G. Subramaniam, W. W. Webb, X.-L. Wu, and C. Xu, "Design of organic molecules with large two-photon absorption cross sections," Science 281, 1653-1656 (1998).
10. L. Ventelon, L. Moreaux, J. Mertz, and M. Blanchard-Desce, "New quadrupolar fluorophores with high two-photon excited fluorescence," Chem. Commun., 2055-2056 (1999).
11. J. Segal, Z. Kotler, M. Sigalov, A. Ben-Asuly, and V. Khodorkovsky, "Two-photon absorption properties of (N-carbazolyl)-stilbenes," Proc. SPIE 3796, 153-159 (1999).
12. O.-K. Kim, K.-S. Lee, H. Y. Woo, K.-S. Kim, G. S. He, J. Swiatkiewicz, and P. N. Prasad, "New class of two-photon-absorbing chromophores based on dithienothiophene," Chem. Mater. 12, 284-286 (2000).
13. S. Delysse, P. Raimond, and J.-M. Nunzi, "Two-photon absorption in non-centrosymmetric dyes," Chem. Phys. 219, 341-351 (1997).
14. P. A. Fleitz, M. C. Brant, R. L. Sutherland, F. P. Strohkendl, R. J. Larsen, and L. R. Dalton, "Nonlinear measurements on AF-50," Proc. SPIE 3472, 91-97 (1998).
15. K. D. Belfield, D. J. Hagan, E. W. Van Stryland, K. J. Schafer, and R. A. Negres, "New two-photon absorbing fluorene derivatives: Synthesis and nonlinear optical characterization," Org. Lett. 1, 1575-1578 (1999).
16. L. Antonov, K. Kamada, K. Ohta, and F. S. Kamounah, "A systematic study on the two-photon absorbing D-π-A molecules-π-bridge nitrogen insertion and strength of the donor and acceptor groups," Phys. Chem. Chem. Phys. 5, 1193-1197 (2003).
17. M. Rumi, J. E. Ehrlich, A. A. Heikal, J. W. Perry, S. Barlow, Z. Hu, D. McCord-Maughon, T. C. Parker, H. Röckel, S. Thayumanavan, S. R. Marder, D. Beljonne, and J.-L. Brédas, "Structure-property relationships for two-photon absorbing chromophores: bis-donor diphenylpolyene and bis(styryl)benzene derivatives," J. Am. Chem. Soc. 122, 9500-9510 (2000).
18. L. Ventelon, S. Charier, L. Moreaux, J. Mertz, and M. Blanchard-Desce, "Nanoscale push-pull dihydrophenanthrene derivatives as novel fluorophores for two-photon-excited fluorescence," Angew. Chem. Int. Ed. 40, 2098-2101 (2001).
19. B. Strehmel, A. M. Sarker, and H. Detert, "The influence of a and n acceptors on two-photon absorption and solvatochromism of dipolar and quadrupolar unsaturated organic compounds," ChemPhysChem 4, 249-259 (2003).
20. T.-C. Lin, G. S. He, P. N. Prasad, and L.-S. Tan, "Degenerate nonlinear absorption and optical power limiting properties of asymmetrically substituted stilbenoid chromophores," J. Mater. Chem. 14, 982-991 (2004).
21. A. R. Morales, K. D. Belfield, J. M. Hales, E. W. Van Stryland, and D. J. Hagan, "Synthesis of two-photon absorbing unsymmetrical fluorenyl-based chromophores," Chem. Mater. 18, 4972-4980 (2006).
22. S.-J. Chung, K.-S. Kim, T.-C. Lin, G. S. He, J. Swiatkiewicz, and P. N. Prasad, "Cooperative enhancement of two-photon absorption in multi-branched structures," J. Phys. Chem. B 103, 10741-10745 (1999).
23. J. Yoo, S. K. Yang, M.-Y. Jeong, H. C. Ahn, S.-J. Jeon, and B. R. Cho, "Bis-1,4-(p-diarylaminostyryl)-2,5-dicyanobenzene derivatives with large two-photon absorption cross-sections," Org. Lett. 5, 645-648 (2003).
24. W. J. Yang, C. H. Kim, M.-Y. Jeong, S. K. Lee, M. J. Piao, S.-J. Jeon, and B. R. Cho, "Synthesis and two-photon absorption properties of 9,10-bis(arylethynyl)anthracene derivatives," Chem. Mater. 16, 2783-2789 (2004).
25. G. P. Bartholomew, M. Rumi, S. J. K. Pond, J. W. Perry, S. Tretiak, and G. C. Bazan, "Two-photon absorption in three-dimensional chromophores based on [2.2]-paracyclophane," J. Am. Chem. Soc. 126, 11529-11542 (2004).
26. C. Katan, F. Terenziani, O. Mongin, M. H. V. Werts, L. Porrès, T. Pons, J. Mertz, S. Tretiak, and M. Blanchard-Desce, "Effects of (multi)branching of dipolar chromophores on physical properties and two-photon absorption," J. Phys. Chem. A 109, 3024-3037 (2005).
27. M. G. Kuzyk, "Fundamental limits on two-photon absorption cross sections," J. Chem. Phys. 119, 8327-8334 (2003).
28. A. Adronov, J. M. J. Fréchet, G. S. He, K.-S. Kim, S.-J. Chung, J. Swiatkiewicz, and P. N. Prasad, "Novel two-photon absorbing dendritic structures," Chem. Mater. 12, 2838-2841 (2000).
29. M. Drobizhev, A. Karotki, A. Rebane, and C. W. Spangler, "Dendrimer molecules with record large two-photon absorption cross section," Opt. Lett. 26, 1081-1083 (2001).
30. O. Mongin, J. Brunel, L. Porrès, and M. Blanchard-Desce, "Synthesis and two-photon absorption of triphenylbenzene-cored dendritic chromophores," Tetrahedron Lett. 44, 2813-2816 (2003).
31. M. Drobizhev, A. Karotki, Y. Dzenis, A. Rebane, Z. Suo, and C. W. Spangler, "Strong cooperative enhancement of two-photon absorption in dendrimers," J. Phys. Chem. B 107, 7540-7543 (2003).
32. M. Drobizhev, A. Rebane, Z. Suo, and C. W. Spangler, "One-, two- and three-photon spectroscopy of π-conjugated dendrimers: cooperative enhancement and coherent domains," J. Lumines. 111, 291-305 (2005).
33. L. Porrès, C. Katan, O. Mongin, T. Pons, J. Mertz, and M. Blanchard-Desce, "Two-photon absorption and fluorescence in nanoscale multipolar chromophores: effect of dimensionality and charge-symmetry," J. Mol. Struct. 704, 17-24 (2004).
34. S. J. K. Pond, M. Rumi, M. D. Levin, T. C. Parker, D. Beljonne, M. W. Day, J.-L. Brédas, S. R. Marder, and J. W. Perry, "One- and two-photon spectroscopy of donor-acceptor-donor distyrylbenzene derivatives: effect of cyano substitution and distorsion from planarity," J. Phys. Chem. A 106, 11470-11480 (2002).
35. M. Rumi, S. J. K. Pond, T. Meyer-Friedrichsen, Q. Zhang, M. Bishop, Y. Zhang, S. Barlow, S. R. Marder, and J. W. Perry, "Tetrastyrylarene derivatives: comparison of one- and two-photon spectroscopic properties with distyrylarene analogues," J. Phys. Chem. C, to be published, manuscript ID jp-2007-10682z.
36. C. Xu, and W. W. Webb, "Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm," J. Opt. Soc. Am. B 13, 481-491 (1996).
37. J. C. Collette, and A. W. Harper, "Chemically-responsive fluorophores exhibiting large color changes," Proc. SPIE 4809, 122-135 (2002).
38. Y. Ren, Q. Xin, X.-T. Tao, L. Wang, X.-Q. Yu, J.-X. Yang, and M.-H. Jiang, "Novel multi-branched organic compounds with enhanced two-photon absorption benefiting from the strong electronic coupling," Chem. Phys. Lett. 414, 253-258 (2005).
39. J. Cornil, D. Beljonne, Z. Shuai, T. W. Hagler, I. Campbell, D. D. C. Bradley, J. L. Brédas, C. W. Spangler, and K. Müllen, "Vibronic structure in the optical absorption spectra of phenylene vinylene oligomers: a joint experimental and theoretical study," Chem. Phys. Lett. 247, 425-432 (1995).
40. M. Kasha, H. R. Rawls, and M. A. El-Bayoumi, "The exciton model in molecular spectroscopy," Pure Appl. Chem. 11, 371-392 (1965).
41. E. G. McRae, and M. Kasha, In Physical Processes in Radiation Biology; Augenstein, L., Mason, R., Rosenberg, B., Eds.; Academic Press, New York, 1964, pp 23-42.
42. D. Beljonne, W. Wenseleers, E. Zojer, Z. Shuai, H. Vogel, S. J. K. Pond, J. W. Perry, S. R. Marder, and J.-L. Brédas, "Role of dimensionality on the two-photon absorption response of conjugated molecules: The case of octupolar compounds," Adv. Funct. Mater. 12, 631-641 (2002).
43. W. G. Fisher, E. A. Wachter, F. E. Lytle, M. Armas, and C. Seaton, "Source-corrected two-photon excited fluorescence measurements between 700 and 880 nm," Appl. Spectrosc. 52, 536-545 (1998).