Acentric nonlinear optical N-benzyl stilbazolium crystals with high environmental stability and enhanced molecular nonlinearity in solid state

Kim, Pil-Joo; Jeong, Jae-Hyeok; Jazbinšek, Mojca; Kwon, SangJoo; Yun, Hoseop; Kim, Jong-Taek; Lee, Yoon Sup; Baek, In Hyung; Rotermund, Fabıan; Günter, Peter; Kwon, O‐Pil

doi:10.1039/c0ce00456a

Cited by 82 publications

(90 citation statements)

References 37 publications

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“…Although the HMQ cation possesses relatively weaker phenolic and methoxy electron donors compared to conventional dimethylamino electron donor,5, 26 the HMQ (OPT) cation with 1‐methylquinolinium electron acceptor exhibit a large maximal first‐order hyperpolarizability β max of 145 ×10 −30 esu, which is similar as for DAST (159 ×10 −30 esu)27 with 1‐methylpyridinium electron acceptor and dimethylamino electron donor, and is higher than in OH1 molecules (104 ×10 −30 esu) 12a. 1‐Methylquinolinium derivatives having the dimethylamino group as electron donor as in DAST exhibit a larger maximal first‐order hyperpolarizability β max (184 × 10 −30 esu).…”

Section: Resultsmentioning

confidence: 91%

Highly Efficient Organic THz Generator Pumped at Near‐Infrared: Quinolinium Single Crystals

Kim

Jeong

Jazbinšek

et al. 2011

Adv Funct Materials

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A novel highly efficient ionic electro‐optic quinolinium single crystals for THz wave applications is reported. Acentric quinolinium derivatives, HMQ‐T (2‐(4‐hydroxy‐3‐methoxystyryl)‐1‐methylquinolinium 4‐methylbenzenesulfonate) and HMQ‐MBS (2‐(4‐hydroxy‐3‐methoxystyryl)‐1‐methylquinolinium 4‐methoxybenzenesulfonate) exhibit high order parameters cos3θp = 0.92 and cos3θp = 1.0, respectively, as well as a large macroscopic optical nonlinearity, which is in the range of the benchmark stilbazolium DAST (N,N‐dimethylamino‐N’‐methylstilbazolium 4‐methylbenzenesulfonate) and phenolic polyene OH1 (2‐(3‐(4‐hydroxystyryl)‐5,5‐dimethylcyclohex‐2‐enylidene)malononitrile) crystals. As‐grown unpolished bulk HMQ‐T crystals with a side length of about 6 mm and thickness of 0.56 mm exhibit 3.1 times higher THz generation efficiency than 0.37 mm thick OH1 crystals and about 8.4 times higher than 1 mm thick inorganic standard ZnTe crystals at the near‐infrared fundamental wavelength of 836 nm. Therefore, HMQ crystals with high order parameter obviously have a very high potential for high power THz‐wave generation and its applications.

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Section: Resultsmentioning

confidence: 91%

Highly Efficient Organic THz Generator Pumped at Near‐Infrared: Quinolinium Single Crystals

Kim

Jeong

Jazbinšek

et al. 2011

Adv Funct Materials

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111

120

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“…Two absorption maxima are observed in organic solvents, one around 500 nm and one upwards of 300 nm . The molecular structure suggests push‐pull behavior in which electrons move from the aniline moiety to its electron‐poor pyridinium group . Fluorescent emission (aqueous solvents) shows a redshift from 470 to 600 nm, suggesting excited‐state relaxation behavior.…”

Section: Long Range Charge Transfer In a Donor‐bridge‐acceptor Dyementioning

confidence: 97%

A quantitative analysis of light‐driven charge transfer processes using voronoi partitioning of time dependent DFT‐derived electron densities

2017

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An analytical method is presented that provides quantitative insight into light-driven electron density rearrangement using the output of standard time-dependent density functional theory (TD-DFT) computations on molecular compounds. Using final and initial electron densities for photochemical processes, the subtraction of summed electron density in each atomcentered Voronoi polyhedron yields the electronic charge difference, Q VECD . This subtractive method can also be used with Bader, Mulliken and Hirshfeld charges. A validation study shows Q VECD to have the most consistent performance across basis sets and good conservation of charge between electronic states. Besides vertical transitions, relaxation processes can be investigated as well. Significant electron transfer is computed for isomerization on the excited state energy surface of azobenzene. A number of linear anilinepyridinium donor-bridge-acceptor chromophores was examined using Q VECD to unravel the influence of its pi-conjugated bridge on charge separation. Finally, the usefulness of the presented method as a tool in optimizing charge transfer is shown for a homologous series of organometallic pigments. The presented work allows facile calculation of a novel, relevant quantity describing charge transfer processes at the atomic level.

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“…Furthermore, the b 0 value of 183 Â 10 À30 esu obtained for DAST is in excellent agreement with the values obtained from quantum chemical calculations in the gas and solid phases (150-194 Â 10 À30 esu ) as reported in Refs. [31,32]. The b 0 value for DA-DMQ1,4-T is~40%…”

Section: Electron-withdrawing Strengthsmentioning

confidence: 98%

“…For example, the well-known and widely applied styryl pyridinium analogue DAST (4-(4-(dimethylamino)styryl)-1-methylpyridinium 4-methylbenzenesulfonate) [25,26] e having a pyridinium electron acceptor (see Fig. 1a) e exhibits a large molecular optical nonlinearity with a high static first hyperpolarizability b 0 of 150-194 Â 10 À30 esu [31,32] and derivatives which are soluble in water as well as organic solvents have been developed [24]. Recently, a quinolinium electron acceptor group has been introduced [33e38].…”

Section: Introductionmentioning

confidence: 99%

N-Methylquinolinium derivatives for photonic applications: Enhancement of electron-withdrawing character beyond that of the widely-used N-methylpyridinium

et al. 2015

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Acentric nonlinear optical N-benzyl stilbazolium crystals with high environmental stability and enhanced molecular nonlinearity in solid state

Cited by 82 publications

References 37 publications

Highly Efficient Organic THz Generator Pumped at Near‐Infrared: Quinolinium Single Crystals

Highly Efficient Organic THz Generator Pumped at Near‐Infrared: Quinolinium Single Crystals

A quantitative analysis of light‐driven charge transfer processes using voronoi partitioning of time dependent DFT‐derived electron densities

N-Methylquinolinium derivatives for photonic applications: Enhancement of electron-withdrawing character beyond that of the widely-used N-methylpyridinium

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