Computational design of benzothiazole-derived push–pull dyes with high molecular quadratic hyperpolarizabilities

Peter Hrobarik; Pavol Zahradnik; Walter M. F. Fabian

doi:10.1039/B314150K

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Computational design of benzothiazole-derived push–pull dyes with high molecular quadratic hyperpolarizabilities†

Peter Hrobarik,^a Pavol Zahradnik^a and Walter M. F. Fabian*^b

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* Corresponding authors

^a Department of Organic Chemistry, Comenius University Bratislava, Mlynská dolina, Bratislava, Slovakia
E-mail: organika@fns.uniba.sk
Fax: ++421-7-729-064
Tel: ++421-7-60296603

^b Institut für Chemie (IfC), Karl-Franzens Universität Graz, Heinrichstr. 28, A-8010 Graz, Austria
E-mail: walter.fabian@uni-graz.at
Fax: ++43-316-380-9840
Tel: ++43-316-380-8636

Abstract

Semi-empirical ZINDO SOS and ab initio quadratic response function (DDRPA) calculations on a series of donor–acceptor substituted π-conjugated chromophores based on styryl benzothiazoles are used to aid in the design of dyes with high non-linear optical properties. Structural modifications studied include nature and position of the donor and/or acceptor group as well as the length of the connecting π-bridge. The most worthwhile target for synthesis are 2-tricyanovinyl-6-p-donor-styryl benzothiazoles and heteroaryl derivatives thereof.

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Supplementary files

Table S1: Heats of formation and relevant torsional angles (AM1) and ZINDO (gas phase and dioxane solution) dipole moments and β _vec-values for different conformations of compounds 1– 51. Table S2: B3LYP/6-31G* energies, zero point energy corrections (au), torsional angles, DRRPA-HF/6-31G* and ZINDO (gas phase) hyperpolarizabilities for different conformations. Table S3: Contributions (two-state model, other configurations) to ZINDO gas phase hyperpolarizabilities (B3LYP/6-31G* lowest energy conformation). Table S4: Orbital energies and coefficients (2p _z, 3p z ) of the two highest occupied and two lowest virtual orbitals of pertinent model compounds. Table S5: Main configurations (gas phase, ZINDO, B3LYP/6-31G* geometry), wavenumbers ν, oscillator strengths f, and difference Δ μ of dipole moment for the first two electronic transitions (states). Table S6: Main configurations (gas phase, TDDFT/B3LYP/6-31G*//B3LYP/6-31G*), wavenumbers ν and oscillator strengths f for the first few electronic transitions (states) of compounds 1– 4, 16, 42 and 48– 50. Table S7: ZINDO SOS results (wavelength λ _max of first absorption band ( f > 0.1), dipole moment μ, and β _vec-values for compounds 1– 51 in the gas phase DOC (1228K)

Article information

DOI: https://doi.org/10.1039/B314150K
Article type: Paper
Submitted: 05 Nov 2003
Accepted: 03 Dec 2003
First published: 06 Jan 2004

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Phys. Chem. Chem. Phys., 2004,6, 495-502

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Computational design of benzothiazole-derived push–pull dyes with high molecular quadratic hyperpolarizabilities

P. Hrobarik, P. Zahradnik and W. M. F. Fabian, Phys. Chem. Chem. Phys., 2004, 6, 495 DOI: 10.1039/B314150K

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Physical Chemistry Chemical Physics

Computational design of benzothiazole-derived push–pull dyes with high molecular quadratic hyperpolarizabilities†

Abstract

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Computational design of benzothiazole-derived push–pull dyes with high molecular quadratic hyperpolarizabilities

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