Supramolecular Second-Order Nonlinearity of Polymers with Orientationally Correlated Chromophores

Kauranen, Martti; Verbiest, Thierry; Boutton, Thomas W.; Teerenstra, M.N.; Clays, Koen; Schouten, A.J.; Nolte, Roeland J. M.; Persoons, André

doi:10.1126/science.270.5238.966

Cited by 182 publications

(133 citation statements)

References 17 publications

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“…We have shown the validity of this approach for bis-dipolar binaphthyl derivatives [6] poly(isocyanide)s [7], and bacteriorhodopsin [8]. Quantum-chemical calculations and depolarized HRS measurements have shown that for dipolar molecules the hyperpolarizability tensor is dominated by the tensor component along the direction of the charge-transfer [9,10].…”

mentioning

confidence: 99%

Quadratic nonlinear optical properties of correlated chromophores: cyclic 6,6′-dinitro-1,1′-binaphthyl-2,2′-ethers

Hendrickx

Boutton

Clays

et al. 1997

Chemical Physics Letters

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mentioning

confidence: 99%

Quadratic nonlinear optical properties of correlated chromophores: cyclic 6,6′-dinitro-1,1′-binaphthyl-2,2′-ethers

Hendrickx

Boutton

Clays

et al. 1997

Chemical Physics Letters

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“…The prominent functions of these biological components have motivated chemists to design artificial helical architectures (1)(2)(3)(4)(5)(6)(7)(8), which can be used for a variety of applications such as chiral separation (9,10) and sensing (11)(12)(13)(14)(15), asymmetric synthesis (16), liquid crystals (17)(18)(19), nonlinear optics (20,21), and so forth. Recently, a hot issue of chirality has emerged in relation to the helicity of the hexagonal carbon lattice in carbon nanotubes, because it determines the conductive properties of carbon nanotubes (22)(23)(24).…”

mentioning

confidence: 99%

Self-assembled graphitic nanotubes with one-handed helical arrays of a chiral amphiphilic molecular graphene

Jin

Fukushima²,

Niki³

et al. 2005

Proc. Natl. Acad. Sci. U.S.A.

269

177

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Self-assembly of a Gemini-shaped, chiral amphiphilic hexa-perihexabenzocoronene having two chiral oxyalkylene side chains, along with two lipophilic side chains, yields graphitic nanotubes with one-handed helical chirality. The nanotubes are characterized by an extremely high aspect ratio of >1,000 and have a uniform diameter of 20 nm and a wall thickness of 3 nm. The nanotubes with right-and left-handed helical senses were obtained from the (S)-and (R)-enantiomers of the amphiphile, respectively, due to an efficient translation of point chirality into supramolecular helical chirality. The (S)-and (R)-enantiomers coassemble at varying mole ratios to give nanotubes, whose circular dichroism profiles are almost unchanged over a wide range of the enantiomeric excess of the amphiphile (100 -20%). The high level of chirality amplification thus observed indicates a long-range cooperativity in the selfassembling process. In sharp contrast, a hexabenzocoronene amphiphile with chiral lipophilic side chains did not form nanotubular assemblies. The present work demonstrates the majority rule in noncovalent systems and also may provide a synthetic strategy toward realization of molecular solenoids. chirality ͉ self-assembly H elicity is one of the most essential structural elements for certain biomolecules such as peptides and DNA. The prominent functions of these biological components have motivated chemists to design artificial helical architectures (1-8), which can be used for a variety of applications such as chiral separation (9, 10) and sensing (11-15), asymmetric synthesis (16), liquid crystals (17-19), nonlinear optics (20, 21), and so forth. Recently, a hot issue of chirality has emerged in relation to the helicity of the hexagonal carbon lattice in carbon nanotubes, because it determines the conductive properties of carbon nanotubes (22-24). Conductive polymers with helical architectures (25) also have attracted attention in view of the concept of molecular solenoids (26,27), although this concept has yet been a dream of scientists, because there are no molecular objects that fulfill certain requisites for conductivity and helicity. Here, we report an example of conductive tubular objects consisting of one-handed helical arrays of a -stacked chiral molecular graphene. Self-assembly of hexa-peri-hexabenzocoronene (HBC) derivatives to form discotic liquid crystals and nanofibers has been studied extensively by Müllen and coworkers (28,29). We recently found that an amphiphilic HBC derivative (1) (Fig. 1) self-assembles in polar organic solvents such as tetrahydrofuran (THF) to give graphitic nanotubes, whose wall consists of a bilayer tape formed from bilaterally coupled columns of -stacked HBC units (30). In the course of this work, we have noticed that the self-assembly of 1, although achiral, gives a mixture of coiled and tubular assemblies under certain conditions, suggesting that the tubular objects also bear a helical structural element. This observation prompted us to design chiral HBC amphiphiles 2 and 3 (Fi...

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“…First, the requirements for materials to be used in device applications that utilize nonlinear interactions are very demanding. New approaches to materials research can yield materials with favorable properties compared to traditional nonlinear materials, as shown recently in several supramolecular systems (Cox et al 1990;Stucky and MacDougall 1990;Clays et al 1993;Kelderman et al 1993;Kauranen et al 1995;Lehn 1995). This is particularly true for 2nd-order nonlinear optics that require noncentrosymmetric materials (Prasad and Williams 1991).…”

Section: Introductionmentioning

confidence: 97%

Enhanced Second-Order Optical Nonlinearity of Dye Molecules Adsorbed onto Laponite Particles

Boutton

Kauranen

Persoons

et al. 1997

Clays and clay miner.

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Nonlinear-optical investigations of new materials are important for 2 complementary reasons. first, the requirements for materials to be used in device applications that utilize nonlinear interactions are very demanding. New approaches to materials research can yield materials with favorable properties compared to traditional nonlinear materials, as shown recently in several supramolecular systems (Cox et a1. 1990; Stucky and MacDougall 1990; Clays et a1. 1993; Kelderman et a1. 1993; Kauranen et a1. 1995; Lehn 1995). This is particularly true for 2nd-order nonlinear optics that require noncentrosymmetric materials (Prasad and Williams 1991). On the other hand. nonlinear-optical processes can provide new techniques to study the properties of new materials. The nonlinear techniques have the potential of being more sensitive than the existing techniques or providing information that is not accessible at all using the existing techniques (Shen 1984). Here again, 2nd-order processes are particularly important because they provide an extremely sensitive tool to study symmetry properties of materials.

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Supramolecular Second-Order Nonlinearity of Polymers with Orientationally Correlated Chromophores

Cited by 182 publications

References 17 publications

Quadratic nonlinear optical properties of correlated chromophores: cyclic 6,6′-dinitro-1,1′-binaphthyl-2,2′-ethers

Quadratic nonlinear optical properties of correlated chromophores: cyclic 6,6′-dinitro-1,1′-binaphthyl-2,2′-ethers

Self-assembled graphitic nanotubes with one-handed helical arrays of a chiral amphiphilic molecular graphene

Enhanced Second-Order Optical Nonlinearity of Dye Molecules Adsorbed onto Laponite Particles

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