Title

Characterisation of a dipolar chromophore with third-harmonic generation applications in the near-IR

Authors

Authors

Y. A. Getmanenko; J. M. Hales; M. Balu; J. Fu; E. Zojer; O. Kwon; J. Mendez; S. Thayumanavan; G. Walker; Q. Zhang; S. D. Bunge; J. L. Bredas; D. J. Hagan; E. W. Van Stryland; S. Barlow;S. R. Marder

Comments

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Abbreviated Journal Title

J. Mater. Chem.

Keywords

BOND-LENGTH ALTERNATION; NONLINEAR-OPTICAL-PROPERTIES; CONJUGATED; ORGANIC-MOLECULES; DONOR-ACCEPTOR POLYENES; CRYSTALLINE POLYMORPH; SELECTION; 2-PHOTON ABSORPTION; POLYMETHINE DYES; TELECOMMUNICATIONS; WAVELENGTHS; ELECTRONIC HYPERPOLARIZABILITY; 3RD-ORDER NONLINEARITIES; Chemistry, Physical; Materials Science, Multidisciplinary

Abstract

E-2-Tricyanovinyl-3-n-hexyl-5-[4-{bis(4-n-butylphenyl)amino}-2-methoxystyryl]-thiophene, 1, has previously been used to demonstrate applications relying on frequency tripling of 1.55 mu m light. Here we report the synthesis and chemical characterisation of 1, along with quantum-chemical calculations and additional experimental investigations of its third-order nonlinear properties that give more insight into its frequency tripling properties. Although 1 can be processed into amorphous films, crystals can also be grown by slow evaporation of solutions; the crystal structure determined by X-ray diffraction shows evidence of significant contributions from zwitterionic resonance forms to the ground-state structure, and reveals centrosymmetric packing exhibiting pi-pi and C-H center dot center dot center dot N C interactions. Both solutions and films of 1 exhibit near-infrared two-photon absorption into the low-lying one-photon-allowed state with a peak two-photon cross-section of ca. 290GM(measured using the white-light continuum method with a pump wavelength of 1800 nm) at a transition energy equivalent to degenerate two-photon absorption at ca. 1360 nm; two related chromophores are also found to show comparable near-IR two-photon cross-sections. Closed-aperture Z-scan measurements and quantum-chemical calculations indicate that the nonlinear refractive index and third-harmonic generation properties of 1 are strongly dependent on frequency in the telecommunications range, due the aforementioned two-photon resonance.

Journal Title

Journal of Materials Chemistry

Volume

22

Issue/Number

10

Publication Date

1-1-2012

Document Type

Article

Language

English

First Page

4371

Last Page

4382

WOS Identifier

WOS:000300250200029

ISSN

0959-9428

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