Nonlinear Optics and Chirality

Verbiest, Thierry; Persoons, André

doi:10.1002/0471471895.ch9

Cited by 8 publications

(23 citation statements)

References 44 publications

(88 reference statements)

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“…Owing to their push–pull-substituted aromatic systems, p -nitroaniline derivatives such as G 1 are known to exhibit the second-order nonlinear optical (NLO) properties, when they are arrayed in a noncentrosymmetric (=polar, chiral or both) arrangement 46 48 . Because the molecules of G 1 confined in poly- F are likely to align in helical arrays, as described above, they potentially show second-order NLO properties 1 2 3 4 . Although there have been reported several host systems that induce the NLO output of chromophore guests, most of them contain the contribution of polar structures 46 49 .…”

Section: Resultsmentioning

confidence: 99%

“…When appropriately functionalized molecules are arranged in one-handed helices, they often display intriguing physical phenomena that never occur in centrosymmetric structures, as represented by second harmonic generation (SHG) 1 2 3 4 and piezoelectricity 5 6 7 8 . These helices would also give a clue to pursue unexplored predictions, including molecular solenoid effects 9 10 .…”

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confidence: 99%

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Macroscopic ordering of helical pores for arraying guest molecules noncentrosymmetrically

Cho

Yamada

et al. 2015

Nat Commun

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Helical nanostructures have attracted continuous attention, not only as media for chiral recognition and synthesis, but also as motifs for studying intriguing physical phenomena that never occur in centrosymmetric systems. To improve the quality of signals from these phenomena, which is a key issue for their further exploration, the most straightforward is the macroscopic orientation of helices. Here as a versatile scaffold to rationally construct this hardly accessible structure, we report a polymer framework with helical pores that unidirectionally orient over a large area (∼10 cm2). The framework, prepared by crosslinking a supramolecular liquid crystal preorganized in a magnetic field, is chemically robust, functionalized with carboxyl groups and capable of incorporating various basic or cationic guest molecules. When a nonlinear optical chromophore is incorporated in the framework, the resultant complex displays a markedly efficient nonlinear optical output, owing to the coherence of signals ensured by the macroscopically oriented helical structure.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Macroscopic ordering of helical pores for arraying guest molecules noncentrosymmetrically

Cho

Yamada

et al. 2015

Nat Commun

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“…Continuous performance improvements of various devices strongly rely on the discovery of new materials with excellent and unique properties. As a consequence, much effort has been made to design and synthesize various functional materials with desirable properties. − Among them, chiral compounds − have drawn great attention due to not only the importance of fundamental science but also the wide range of practical applications in such areas as catalysis, medicine, polymer, materials science, molecular devices, and nonlinear optics. − In particular, chiral compounds exhibit a unique advantage (i.e., inherent asymmetric structures) for the second-order nonlinear optical (NLO) materials, making it so that their second-order NLO response could be detected even in highly symmetric media, such as chiral isotropic liquids. − Recently, some chiral compounds with high second-order NLO performance have been discovered. − …”

Section: Introductionmentioning

confidence: 99%

Photophysical Properties of Chiral Tetraphenylethylene Derivatives with the Fixed Propeller-Like Conformation

Liu

Yang

et al. 2018

J. Phys. Chem. C

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The recent synthesized helical tetraphenylethylene (TPE) exhibits broad application prospects such as display, catalysis, and medical imaging. A full understanding of the intricate relation between structure and property is rather important to structural design and performance improvement. Here, we employed density functional theory (DFT) and timedependent DFT to calculate their ground-and excited-state structures, electron transition properties, optical rotation (OR), and second-order nonlinear optical (NLO) properties. For compound 1, the simulated UV−vis/CD spectra and calculated OR value are in reasonable agreement with the experimental ones, allowing us to reliably assign the electron transition and determine the absolute configuration. Intriguingly, TPE derivatives are excellent candidates for the second-order NLO materials in view of the large first hyperpolarizability values and intrinsic asymmetric structures. The intramolecular charge transfer cooperativity for this kind of compound was achieved through involvement of the donor and acceptor substituent groups or their combinations. The charge transfer within TPE plays a key role in determining the chiral origin and electron transition properties, whereas the contribution of peripheral phenyl rings is fairly small. Moreover, the designed compounds 5 and 7 are potential materials for the fluorescent probe.

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“…Besides the merits of organic compounds, chiral organic compounds with intrinsic asymmetric structure exhibit great advantage in second‐order NLO and asymmetry catalysis . Incorporation of chiral substituents at α or meso position of BODIPY is expected to produce chirality in BODIPY derivatives ,.…”

Section: Introductionmentioning

confidence: 99%

Unveiling the Photophysical Properties of Boron Heptaaryldipyrromethene Derivatives

et al. 2018

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Increased interest has been devoted to the discovery of multifunctional materials with desirable properties, as continuous performance enhancement of various devices mainly depends on high-performance materials. Now, density functional theory has become a powerful tool to design new materials and rationalize experimental observations. In this work, we explored the photophysical properties origin of chiral boron heptaaryldipyrromethene (heptaaryl-BODIPY), which has charming optoelectronic properties. At the same time, we designed the other five compounds on the basis of heptaaryl-BODIPY. The simulated electronic absorption and emission spectra of heptaaryl-BODIPY are in agreement with experimental ones, allowing us to reliably assign its electronic transition property. The designed compound 6 shows remarkably large first hyperpolarizability value up to 82.78×10 esu. For this kind of compounds, their NLO response values associate with not only position but also electronic nature of substituent groups. Moreover, electron reorganization energies of compounds 1-4 are comparable to tris(8-hydroxyquinolinato)aluminium(III) which is a typical electron transport material. Intriguingly, the studied compounds are the excellent fluorescent probe materials from the standpoint of large Stokes shift and high emission efficiency. Our work enables an opportunity for understanding the relationship between microelectronic structure and macroscopic performance of BODIPY derivatives.

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Nonlinear Optics and Chirality

Cited by 8 publications

References 44 publications

Macroscopic ordering of helical pores for arraying guest molecules noncentrosymmetrically

Macroscopic ordering of helical pores for arraying guest molecules noncentrosymmetrically

Photophysical Properties of Chiral Tetraphenylethylene Derivatives with the Fixed Propeller-Like Conformation

Unveiling the Photophysical Properties of Boron Heptaaryldipyrromethene Derivatives

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