Helquat Dyes: Helicene-like Push-Pull Systems with Large Second-Order Nonlinear Optical Responses

Benjamin J. Coe; Daniela Rusanova; Vishwas D. Joshi; Sergio Sánchez; Jan Vávra; Dushant Khobragade; Lukáš Severa; Ivana Císařová; David Šaman; Radek Pohl; Koen Clays; Griet Depotter; Bruce S. Brunschwig; Filip Teplý

doi:10.1021/acs.joc.5b02692

Helquat Dyes: Helicene-like Push-Pull Systems with Large Second-Order Nonlinear Optical Responses

Benjamin J. Coe^*, Daniela Rusanova, Vishwas D. Joshi, Sergio Sánchez, Jan Vávra, Dushant Khobragade, Lukáš Severa, Ivana Císařová, David Šaman, Radek Pohl, Koen Clays, Griet Depotter, Bruce S. Brunschwig, Filip Teplý

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

Helquat dyes combine a cationic hemicyanine with a helicene-like motif to form a new blueprint for chiral systems with large and tunable nonlinear optical (NLO) properties. We report a series of such species with characterization, including determination of static first hyperpolarizabilities β₀ via hyper-Rayleigh scattering and Stark spectroscopy. The measured β₀ values are similar to or substantially larger than that of the commercial chromophore E-4′-(dimethylamino)-N-methyl-4-stilbazolium. Density functional theory (DFT) and time-dependent DFT calculations on two of the new cations are used to probe their molecular electronic structures and optical properties. Related molecules are expected to show bulk second-order NLO effects in even nonpolar media, overcoming a key challenge in developing useful materials.

Original language	English
Pages (from-to)	1912-1920
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	81
Issue number	5
DOIs	https://doi.org/10.1021/acs.joc.5b02692
Publication status	Published - 4 Mar 2016

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10.1021/acs.joc.5b02692

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Coe, B. J., Rusanova, D., Joshi, V. D., Sánchez, S., Vávra, J., Khobragade, D., Severa, L., Císařová, I., Šaman, D., Pohl, R., Clays, K., Depotter, G., Brunschwig, B. S., & Teplý, F. (2016). Helquat Dyes: Helicene-like Push-Pull Systems with Large Second-Order Nonlinear Optical Responses. Journal of Organic Chemistry, 81(5), 1912-1920. https://doi.org/10.1021/acs.joc.5b02692

@article{6364010d4fa54963b72092a8beb891be,

title = "Helquat Dyes: Helicene-like Push-Pull Systems with Large Second-Order Nonlinear Optical Responses",

abstract = "Helquat dyes combine a cationic hemicyanine with a helicene-like motif to form a new blueprint for chiral systems with large and tunable nonlinear optical (NLO) properties. We report a series of such species with characterization, including determination of static first hyperpolarizabilities β0 via hyper-Rayleigh scattering and Stark spectroscopy. The measured β0 values are similar to or substantially larger than that of the commercial chromophore E-4′-(dimethylamino)-N-methyl-4-stilbazolium. Density functional theory (DFT) and time-dependent DFT calculations on two of the new cations are used to probe their molecular electronic structures and optical properties. Related molecules are expected to show bulk second-order NLO effects in even nonpolar media, overcoming a key challenge in developing useful materials.",

author = "Coe, {Benjamin J.} and Daniela Rusanova and Joshi, {Vishwas D.} and Sergio S{\'a}nchez and Jan V{\'a}vra and Dushant Khobragade and Luk{\'a}{\v s} Severa and Ivana C{\'i}sa{\v r}ov{\'a} and David {\v S}aman and Radek Pohl and Koen Clays and Griet Depotter and Brunschwig, {Bruce S.} and Filip Tepl{\'y}",

year = "2016",

month = mar,

day = "4",

doi = "10.1021/acs.joc.5b02692",

language = "English",

volume = "81",

pages = "1912--1920",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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Coe, BJ, Rusanova, D, Joshi, VD, Sánchez, S, Vávra, J, Khobragade, D, Severa, L, Císařová, I, Šaman, D, Pohl, R, Clays, K, Depotter, G, Brunschwig, BS & Teplý, F 2016, 'Helquat Dyes: Helicene-like Push-Pull Systems with Large Second-Order Nonlinear Optical Responses', Journal of Organic Chemistry, vol. 81, no. 5, pp. 1912-1920. https://doi.org/10.1021/acs.joc.5b02692

TY - JOUR

T1 - Helquat Dyes

T2 - Helicene-like Push-Pull Systems with Large Second-Order Nonlinear Optical Responses

AU - Coe, Benjamin J.

AU - Rusanova, Daniela

AU - Joshi, Vishwas D.

AU - Sánchez, Sergio

AU - Vávra, Jan

AU - Khobragade, Dushant

AU - Severa, Lukáš

AU - Císařová, Ivana

AU - Šaman, David

AU - Pohl, Radek

AU - Clays, Koen

AU - Depotter, Griet

AU - Brunschwig, Bruce S.

AU - Teplý, Filip

PY - 2016/3/4

Y1 - 2016/3/4

N2 - Helquat dyes combine a cationic hemicyanine with a helicene-like motif to form a new blueprint for chiral systems with large and tunable nonlinear optical (NLO) properties. We report a series of such species with characterization, including determination of static first hyperpolarizabilities β0 via hyper-Rayleigh scattering and Stark spectroscopy. The measured β0 values are similar to or substantially larger than that of the commercial chromophore E-4′-(dimethylamino)-N-methyl-4-stilbazolium. Density functional theory (DFT) and time-dependent DFT calculations on two of the new cations are used to probe their molecular electronic structures and optical properties. Related molecules are expected to show bulk second-order NLO effects in even nonpolar media, overcoming a key challenge in developing useful materials.

AB - Helquat dyes combine a cationic hemicyanine with a helicene-like motif to form a new blueprint for chiral systems with large and tunable nonlinear optical (NLO) properties. We report a series of such species with characterization, including determination of static first hyperpolarizabilities β0 via hyper-Rayleigh scattering and Stark spectroscopy. The measured β0 values are similar to or substantially larger than that of the commercial chromophore E-4′-(dimethylamino)-N-methyl-4-stilbazolium. Density functional theory (DFT) and time-dependent DFT calculations on two of the new cations are used to probe their molecular electronic structures and optical properties. Related molecules are expected to show bulk second-order NLO effects in even nonpolar media, overcoming a key challenge in developing useful materials.

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DO - 10.1021/acs.joc.5b02692

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SN - 0022-3263

VL - 81

SP - 1912

EP - 1920

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 5

ER -

Helquat Dyes: Helicene-like Push-Pull Systems with Large Second-Order Nonlinear Optical Responses

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CCDC 1012247: Experimental Crystal Structure Determination

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Helquat Dyes: Helicene-like Push-Pull Systems with Large Second-Order Nonlinear Optical Responses

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CCDC 1012247: Experimental Crystal Structure Determination

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