Extended squaraine dyes with large two-photon absorption cross-sections

Journal of the American Chemical Society

Volumn 128, Issue 45, 2006, Pages 14444-14445

  Chung, Sung Jae ^a   Zheng, Shijun ^a   Odani, Toru ^a   Beverina, Luca ^a,b   Fu, Jie ^c   Padilha, Lazaro A ^c,e   Biesso, Arianna ^a   Hales, Joel M ^a   Zhan, Xiaowei ^a   Schmidt, Karin ^a   Ye, Aijun ^a   Zojer, Egbert ^a,f   Barlow, Stephen ^a   Hagan, David J ^c   Van Stryland, Eric W ^c   Yi, Yuanping ^d   Shuai, Zhigang ^d   Pagani, Giorgio A ^b   Brédas, Jean Luc ^a   Perry, Joseph W ^a   Marder, Seth R ^a   more..

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

^c UNIVERSITY OF CENTRAL FLORIDA   (United States)

^d INSTITUTE OF CHEMISTRY   (China)

^e UNIVERSITY OF CAMPINAS   (Brazil)

^f GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

DYE; SQUARAINE; SQUARAINE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; PHOTON; SYNTHESIS;

EID: 33750971746     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065556m     Document Type: Article

References (20)

1. Lin, T.-Z.; Chung, S.-J.; Kim, K.-S.; Wang, X.; He, G. S.; Swiatkiewicz, J.; Pudavar, H. E.; Prasad, P. N. Adv. Polym. Sci. 2003, 161, 157.
2. (a) Albota, M. et al. Science 1998, 281, 1653.
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4. (c) Strehmel, B.; Sarker, A. M.; Detert, H. ChemPhysChem 2003, 4, 249.
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7. Other squaraine oligomers are known, including examples with pyrrole-squaraine links like to those in 1-5; for example, see Ajayaghosh, A.; Eldo, J. Org. Lett. 2001, 3, 2595 and references therein.
8. Sheik-bahae, M.; Said, A. A.; Van Stryland, E. W. Opt. Lett. 1989, 14, 955.
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12. The values quoted refer to MRD-CI calculations with an MO-active space of 7/7 for 1 and 11/9 for 3, respectively The impact of the choice of the Cl-active space, a comparison between CCSD and MRD-CI calculations as well as a brief discussion of conformers can be found in the Supporting Information.
13. (3) and γ are defined here as in Butcher, P. N.; Cotter, D. The Elements of Nonlinear Optics; Cambridge University Press: Cambridge, 1990.
14. (3) and γ for squaraines and for discussion of the role of 2PA resonances upon these quantities see (a) Dirk, C. W.; Kuzyk, M. G. Chem. Mater. 1980, 2, 4.
15. (b) Dirk, C. W.; Herndon, W. C.; Cervantes-Lee, F.; Selnau, H.; Martinez, S.; Kalamegham, P.; Tan, A.; Campos, G.; Velez, M.; Zyss, J.; Ledoux, I.; Cheng, L.-T. J. Am. Chem. Soc. 1995, 117, 2214.
16. -11 esu from degenerate four-wave mixing.
17. Differences between solution and solid-state values are likely to be due to local-field effects.
18. There are only a few reports of strong 2PA in this range: (a) Beverina, L.; Fu, J.; Leclercq, A.; Zojer, E.; Pacher, P.; Barlow, S.; Van Stryland, E. W.; Hagan, D. J.; Brédas, J.-L.; Marder, S. R. J. Am. Chem. Soc. 2005, 127, 7282.
19. (b) Kurotobi, K.; Kim, K. S.; Noh, S. B.; Kim, D.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45, 3944.
20. g state, for which small δ (< 100 GM) are calculated for 1 and 3 (see Supporting Information).