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

Yulia A. Getmanenko; Joel M. Hales; Mihaela Balu; Jie Fu; Egbert Zojer; Ohyun Kwon; Jeffrey Mendez; S. Thayumanavan; Gregory Walker; Qing Zhang; Scott D. Bunge; Jean-Luc Brédas; David J. Hagan; Eric W. Van Stryland; Stephen Barlow; Seth R. Marder

doi:10.1039/C2JM15599K

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Journal of Materials Chemistry

Issue 10, 2012

Journal of Materials Chemistry was published between 1991 and 2012. From issue 1, 2013, it was replaced by three new journals: Journal of Materials Chemistry A, B and C

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Paper

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

Yulia A. Getmanenko,^a Joel M. Hales,^b Mihaela Balu,^b Jie Fu,^b Egbert Zojer,^a^c Ohyun Kwon,^a Jeffrey Mendez,^d S. Thayumanavan,^d Gregory Walker,^e Qing Zhang,^a Scott D. Bunge,^f Jean-Luc Brédas,^a David J. Hagan,^b Eric W. Van Stryland,^b Stephen Barlow^a^e and Seth R. Marder^a^d^e

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School of Chemistry and Biochemistry and Center for Organic Photonics and Electronics, Georgia Institute of Technology, Atlanta, USA

CREOL & FPCE, The College of Optics and Photonics and Department of Physics, University of Central Florida, Orlando

Institute of Solid State Physics, Graz University of Technology, Graz, Austria

Beckman Institute, California Institute of Technology, Pasadena, USA

Department of Chemistry, University of Arizona, Tucson, USA

Department of Chemistry and Biochemistry, Kent State University, Kent, USA

J. Mater. Chem., 2012,22, 4371-4382

DOI: 10.1039/C2JM15599K
Received 01 Nov 2011, Accepted 01 Dec 2011
First published online 10 Jan 2012

This article is part of themed collection: Organic optoelectronic materials

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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 μm 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 π–π and C–HN [triple bond, length as m-dash] 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. 290 GM (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.