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

Coe, Benjamin J. and Rusanova, Daniela and Joshi, Vishwas D. and Sánchez, Sergio and Vávra, Jan and Khobragade, Dushant and Severa, Lukáš and Císařová, Ivana and Šaman, David and Pohl, Radek and Clays, Koen and Depotter, Griet and Brunschwig, Bruce S. and Teplý, Filip (2016) Helquat Dyes: Helicene-like Push–Pull Systems with Large Second-Order Nonlinear Optical Responses. Journal of Organic Chemistry, 81 (5). pp. 1912-1920. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20160316-082203585

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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 β_0 via hyper-Rayleigh scattering and Stark spectroscopy. The measured β_0 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/acs.joc.5b02692DOIArticle
http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b02692PublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/acs.joc.5b02692PublisherSupporting Information
ORCID:
AuthorORCID
Coe, Benjamin J.0000-0002-5998-3895
Brunschwig, Bruce S.0000-0002-6135-6727
Additional Information:© 2016 American Chemical Society. ACS AuthorChoice - This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. Received: December 2, 2015; Published: February 4, 2016. This work was supported by ASCR (RVO: 61388963, M200551208 to F.T.), the Czech Science Foundation (13-19213S to F.T.), the Fund for Scientific Research-Flanders (Research Grant 1510712N), the University of Leuven (GOA/2011/03), and the EPSRC (grants EP/G020299/1 and EP/J018635/1 to B.J.C.). B.S.B. acknowledges the Beckman Institute of the California Institute of Technology for support. We thank Mrs. J. Bařinková for her skillful experimental help. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
Academy of Sciences of the Czech Republic61388963
Academy of Sciences of the Czech RepublicM200551208
Czech Science Foundation13-19213S
Fonds Wetenschappelijk Onderzoek - Vlaanderen (FWO)1510712N
University of LeuvenGOA/2011/03
Engineering and Physical Sciences Research Council (EPSRC)EP/G020299/1
Engineering and Physical Sciences Research Council (EPSRC)EP/J018635/1
Caltech Beckman InstituteUNSPECIFIED
Issue or Number:5
Record Number:CaltechAUTHORS:20160316-082203585
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160316-082203585
Official Citation: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, and Filip Teplý The Journal of Organic Chemistry 2016 81 (5), 1912-1920 DOI: 10.1021/acs.joc.5b02692
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:65386
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:16 Mar 2016 16:29
Last Modified:03 Oct 2019 09:46

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