A series of highly efficient and thermally stable second-order nonlinear optical (NLO) dipolar donorauxiliary donor-acceptor chromophores have been synthesised in which a hydrazono group and a pyrrole ring act as donor and auxiliary donor components, respectively, in combination with different aromatic and heteroaromatic acceptors. The new dyes have been systematically investigated by NMR spectroscopy, absorption spectroscopy, NLO measurements and thermal stability studies. NLO properties have been studied in detail by electrooptical absorption (EOA) and hyperRayleigh scattering (HRS) measurements in 1,4-dioxane and DMSO, respectively. The results originating from the two different methods have been compared and analysed in detail. We found that the NLO properties mea-sured by the EOA and HRS methods correlate with each other and converge to reveal the dye with the acceptor 2dicyanomethylene-3-cyano-4,5, 5-trimethyl-2,5-dihydrofuran as the most efficient system, The unprecedented combination of a strong donor hydrazono group and the auxiliary donor effects of π-excessive heteroaromatic rings afforded NLO chromophores with very high values (ju,J}ü(EOA) up to 2038xl0-48esu and β(HRS) up to 398OxIO-30 esu at 1.5 urn). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA,.
Abbotto, A., Beverina, L., Manfredi, N., Pagani, G., Archetti, G., Kuball, H., et al. (2009). Second-Order Nonlinear Optical Activity of Dipolar Chromophores Based on Pyrrole-Hydrazono Donor Moieties. CHEMISTRY-A EUROPEAN JOURNAL, 15(25), 6175-6185 [10.1002/chem.200900287].
Second-Order Nonlinear Optical Activity of Dipolar Chromophores Based on Pyrrole-Hydrazono Donor Moieties
ABBOTTO, ALESSANDRO;BEVERINA, LUCA;MANFREDI, NORBERTO;PAGANI, GIORGIO ALBERTO;
2009
Abstract
A series of highly efficient and thermally stable second-order nonlinear optical (NLO) dipolar donorauxiliary donor-acceptor chromophores have been synthesised in which a hydrazono group and a pyrrole ring act as donor and auxiliary donor components, respectively, in combination with different aromatic and heteroaromatic acceptors. The new dyes have been systematically investigated by NMR spectroscopy, absorption spectroscopy, NLO measurements and thermal stability studies. NLO properties have been studied in detail by electrooptical absorption (EOA) and hyperRayleigh scattering (HRS) measurements in 1,4-dioxane and DMSO, respectively. The results originating from the two different methods have been compared and analysed in detail. We found that the NLO properties mea-sured by the EOA and HRS methods correlate with each other and converge to reveal the dye with the acceptor 2dicyanomethylene-3-cyano-4,5, 5-trimethyl-2,5-dihydrofuran as the most efficient system, The unprecedented combination of a strong donor hydrazono group and the auxiliary donor effects of π-excessive heteroaromatic rings afforded NLO chromophores with very high values (ju,J}ü(EOA) up to 2038xl0-48esu and β(HRS) up to 398OxIO-30 esu at 1.5 urn). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA,.
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