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Tunable Chiral Second-Order Nonlinear Optical Chromophores Based on Helquat Dications

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    SYSNO ASEP0478612
    Document TypeJ - Journal Article
    R&D Document TypeJournal Article
    Subsidiary JČlánek ve WOS
    TitleTunable Chiral Second-Order Nonlinear Optical Chromophores Based on Helquat Dications
    Author(s) Buckley, L. E. R. (GB)
    Coe, B. J. (GB)
    Rusanova, D. (GB)
    Joshi, Vishwas (UOCHB-X) RID
    Sánchez, S. (GB)
    Jirásek, Michael (UOCHB-X) RID
    Vávra, Jan (UOCHB-X) RID
    Khobragade, Dushant (UOCHB-X)
    Severa, Lukáš (UOCHB-X) RID, ORCID
    Císařová, I. (CZ)
    Šaman, David (UOCHB-X) RID, ORCID
    Pohl, Radek (UOCHB-X) RID, ORCID
    Clays, K. (BE)
    Depotter, G. (BE)
    Brunschwig, B. S. (US)
    Teplý, Filip (UOCHB-X) RID, ORCID
    Source TitleJournal of Physical Chemistry A. - : American Chemical Society - ISSN 1089-5639
    Roč. 121, č. 31 (2017), s. 5842-5855
    Number of pages14 s.
    Languageeng - English
    CountryUS - United States
    Keywordshyper-Rayleigh scattering ; excited states ; derivatives
    Subject RIVCF - Physical ; Theoretical Chemistry
    OECD categoryPhysical chemistry
    R&D ProjectsGA13-19213S GA ČR - Czech Science Foundation (CSF)
    NV16-31156A GA MZd - Ministry of Health (MZ)
    Institutional supportUOCHB-X - RVO:61388963
    UT WOS000407656100009
    EID SCOPUS85027271215
    DOI10.1021/acs.jpca.7b06057
    AnnotationFourteen new dipolar cations have been synthesized, containing methoxy or tertiary amino electron donor groups attached to helquat (Hq) acceptors. These Hq derivatives have been characterized as their TfO- salts by using various techniques including NMR and electronic absorption spectroscopies. UV-vis spectra show intense, relatively low energy absorptions with lambda(max) approximate to 400-600 nm, attributable to intramolecular charge-transfer (ICT) excitations. Single-crystal X-ray structures have been solved for two of the chromophores, one as its PF6- salt, revealing centrosymmetric packing arrangements (space groups Pbca and P (1) over bar). Molecular quadratic nonlinear optical (NLO) responses have been determined directly by using hyper-Rayleigh scattering (HRS) with a 800 nm laser, and indirectly via Stark (electroabsorption) spectroscopy for the low energy absorption bands. The obtained static first hyperpolarizabilities beta(0) range from moderate to large: (9-140) X 10(-30) esu from HRS in MeCN and (44-580) X 10(-30) esu from the Stark data in PrCN. The magnitude of beta(0) increases upon either extending the pi-conjugation length or replacing a methoxy with a tertiary amino electron donor substituent. Density functional theory (DFT) and time dependent DFT calculations on selected tertiary amino chromophores confirm that the low energy absorptions have ICT character. Relatively good agreement between the simulated and experimental UV-vis absorption spectra is achieved by using the CAM-B3LYP functional with the 6-311G(d) basis set. The beta(tot) values predicted by using DFT at the same level of theory are large ((472-1443) X 10(-30) esu in MeCN). Both the theoretical and experimental results show that para-conjugation between Hq and electron donor fragments is optimal, and enlarging the Hq unit is inconsequential with respect to the molecular quadratic NLO response.
    WorkplaceInstitute of Organic Chemistry and Biochemistry
    Contactasep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418
    Year of Publishing2018
Number of the records: 1  

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