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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Scopus citations


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-H⋯NC 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.

Original languageEnglish (US)
Pages (from-to)4371-4382
Number of pages12
JournalJournal of Materials Chemistry
Issue number10
StatePublished - Mar 14 2012
Externally publishedYes

ASJC Scopus subject areas

  • General Chemistry
  • Materials Chemistry


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