journal article·2006-06-01

Pyrroline Chromophores for Electro-Optics

Sei-Hum Jang, Jingdong Luo, Neil M. Tucker, Amalia Leclercq, Egbert Zojer, Marnie A. Haller, Tae-Dong Kim, Jae-Wook Kang, Kimberly Firestone, Denise Bale, David Lao, Jason B. Benedict, Dawn Cohen, Werner Kaminsky, Bart Kahr, Jean-Luc Brédas, Philip Reid, Larry R. Dalton, Alex K. -Y. Jen

Chemistry of Materials· Volume 18· Issue 13
Publisher page

Abstract

We have synthesized a new class of highly efficient nonlinear optical (NLO) chromophores based on the novel tricyanopyrroline (TCP) electron acceptor. Molecular linear and nonlinear optical properties of the prototypical chromophores were measured and calculated to understand structure−property relationships. One such chromophore showed molecular first hyperpolarizability (β) of (8700 ± 702) × 10 - 30 esu at excitation wavelengths of 1.9 μm, and another showed macroscopic electro-optic (EO) coefficients ( r 33 ) of 51 pm/V at 1.55 μm with 20 wt % chromophore loading when poled with 65 V/μm in amorphous polycarbonate film. Synthetic strategies for extending the utility of the acceptor and chromophores are discussed.
Source: openalex_inverted_index · Quality: baseline

Research context

OpenAlex topics: Nonlinear Optical Materials Research · Solid-state spectroscopy and crystallography · Chemical synthesis and pharmacological studies

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Departments of Materials Science and Engineering, University of Washington, Seattle, Washington 98195-2120, Department of Chemistry, University of Washington, Seattle, Washington 98195-1700, and School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, Georgia 30332-0400

References (50)

Show source-provided references
1. Ma H. · Adv. Mater. · 2002 · 14 · 133910.1002/1521-4095(20021002)14:19<1339::AID-ADMA1339>3.0.CO;2-O ↗
2. Dalton L. R. · J. Mater. Chem. · 1999 · 9 · 190510.1039/a902659b ↗
3. Dalton L. R. A. · Adv. Mater. · 1995 · 7 · 51910.1002/adma.19950070603 ↗
4. Shi Y. · Science · 2000 · 288 · 11910.1126/science.288.5463.119 ↗
5. Robinson B. H. · Chem. Phys. · 1999 · 245 · 3510.1016/S0301-0104(99)00079-8 ↗
6. Ma H. · Adv. Funct. Mater. · 2002 · 12 · 56510.1002/1616-3028(20020916)12:9<565::AID-ADFM565>3.0.CO;2-8 ↗
7. Luo J. · Adv. Mater. · 2002 · 14 · 176310.1002/1521-4095(20021203)14:23<1763::AID-ADMA1763>3.0.CO;2-U ↗
8. Luo J. · Adv. Mater. · 2003 · 15 · 163510.1002/adma.200305202 ↗
9. Luo J. · J. Phys. Chem. B · 2004 · 108 · 852310.1021/jp036714o ↗
10. Dalton L. R. · J. Chem. Mater. · 1995 · 7 · 106010.1021/cm00054a006 ↗
11. Marder S. R. · Science · 1994 · 263 · 51110.1126/science.263.5146.511 ↗
12. Marder S. R. · Science · 1994 · 265 · 63210.1126/science.265.5172.632 ↗
13. Dalton L. R. · Opt. Eng. · 2000 · 39 · 58910.1117/1.602403 ↗
14. He M. Q. · Chem. Mater. · 2002 · 14 · 466210.1021/cm020405d ↗
15. He M. Q. · Chem. Mater. · 2002 · 14 · 466910.1021/cm0204066 ↗
16. Liu S. · Adv. Mater. · 2003 · 15 · 60310.1002/adma.200304813 ↗
17. Breitbeil F. W. · J. Org. Chem. · 1979 · 44 · 464910.1021/jo00393a038 ↗
18. Hennion G. F. · J. Org. Chem. · 1958 · 23 · 65810.1021/jo01099a003 ↗
19. Fatiadi A. · J. Synthesis · 1978 · 16510.1055/s-1978-24703 ↗
20. Carboni R. A. · J. Am. Chem. Soc. · 1958 · 80 · 283810.1021/ja01544a061 ↗
21. Villemin D. · Synth. Commun. · 2001 · 31 · 177110.1081/SCC-100104407 ↗
22. Zhang C. · Chem. Mater. · 2001 · 13 · 304310.1021/cm010463j ↗
23. Melikian G. · Synth. Commun. · 1995 · 25 · 304510.1080/00397919508011437 ↗
24. Gubler U. · Adv. Mater. · 2002 · 14 · 31310.1002/1521-4095(20020219)14:4<313::AID-ADMA313>3.0.CO;2-9 ↗
25. Carboni R. A. U.S. · 1961
26. Hiroyuki M. · 1989
27. Leslie S. · 1992
28. Denise C. · 1997
29. The · 1987
30. Firestone K. A. · Inorg. Chim. Acta · 2004 · 357 · 395710.1016/j.ica.2004.07.031 ↗
31. Jen A. K.-Y. · J. Chem. Soc., Chem. Commun. · 1993 · 9010.1039/c39930000090 ↗
32. Rao V. P. · J. Tetrahedron Lett. · 1993 · 34 · 174710.1016/S0040-4039(00)60768-2 ↗
33. Structural · Chem. Commun. · 2002 · 8 · 888
34. The · J. Am. Chem. Soc. · 1985 · 107 · 390210.1021/ja00299a024 ↗
35. He M. · 2002
36. Willets K. A. · J. Am. Chem. Soc. · 2003 · 125 · 117410.1021/ja029100q ↗
37. Zhang C. · Chem. Mater. · 2001 · 13 · 304310.1021/cm010463j ↗
38. He M. · Chem. Mater. · 2002 · 14 · 466910.1021/cm0204066 ↗
39. He M. · Chem. Mater. · 2002 · 14 · 466210.1021/cm020405d ↗
40. Paley M. S. · J. Org. Chem. · 1989 · 54 · 377410.1021/jo00277a007 ↗
41. The · J. Am. Chem. Soc. · 1985 · 107 · 390210.1021/ja00299a024 ↗
42. The first-hyperpolarizabilities (β) of chromophores were measured relative to βchloroformand reported with conversion. There are two values for the hyperpolarizability of chloroform in the literature. βchlorofomrof 0.49 × 10-30was used for conversion. Comparison of β for all chromophores at a single excitation wavelength, say 1.9 μm, is not useful because of various resonance effects, resulting from the wide range of spectral windows between chromophores.
43. Würthner F. · J. Am. Chem. Soc. · 2002 · 124 · 943110.1021/ja020168f ↗
44. Wortmann R. · Angew. Chem., Int. Ed. · 2003 · 42 · 208010.1002/anie.200250782 ↗
45. Würthner F. · Angew. Chem., Int. Ed. · 2000 · 39 · 198710.1002/1521-3773(20000602)39:11<1987::AID-ANIE1987>3.0.CO;2-4 ↗
46. Teng C. C. · Appl. Phys. Lett. · 1990 · 56 · 173410.1063/1.103107 ↗
47. Zhang C. · Chem. Mater. · 2001 · 13 · 304310.1021/cm010463j ↗
48. Staub K. · J. Mater. Chem. · 2003 · 13 · 82510.1039/b208024a ↗
49. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R.Purification of LaboratoryChemicals; Pergamon Press: Oxford, 1980; p 77.
50. Zhang C. · Macromolecules · 2001 · 34 · 25310.1021/ma001561d ↗