Self-Assembled Electrooptic Thin Films with Remarkably Blue-Shifted Optical Absorption Based on an X-Shaped Chromophore

Kang, Hee Kap; Zhu, Ping; Yang, Yu; Facchetti, and Antonio; Marks, Tobin J.

doi:10.1021/ja045043k

Cited by 84 publications

(44 citation statements)

References 29 publications

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“…Materials can also be prepared by sequential synthesis/self-assembly techniques and by crystal growth including from solution, the melt and the vapor phase [97][98][99][100][101][102][103][104][105][106][107]; however, these approaches have not been as widely adapted to the fabrication of prototype devices as have electric field poling methods.…”

Section: Advances In Materials Processing and Characterizationmentioning

confidence: 99%

Theory-Guided Design of Organic Electro-Optic Materials and Devices

Dalton

Benight

2011

Polymers

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Integrated (multi-scale) quantum and statistical mechanical theoretical methods have guided the nano-engineering of controlled intermolecular electrostatic interactions for the dramatic improvement of acentric order and thus electro-optic activity of melt-processable organic polymer and dendrimer electro-optic materials. New measurement techniques have permitted quantitative determination of the molecular order parameters, lattice dimensionality, and nanoscale viscoelasticity properties of these new soft matter materials and have facilitated comparison of theoretically-predicted structures and thermodynamic properties with experimentally-defined structures and properties. New processing protocols have permitted further enhancement of material properties and have facilitated the fabrication of complex device structures. The integration of organic electro-optic materials into silicon photonic, plasmonic, and metamaterial device architectures has led to impressive new performance metrics for a variety of technological applications.

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Section: Advances In Materials Processing and Characterizationmentioning

confidence: 99%

Theory-Guided Design of Organic Electro-Optic Materials and Devices

Dalton

Benight

2011

Polymers

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“…Among them, cruciform-shaped molecules exhibit spatial separation of their frontier molecular orbitals, building 1,2,4,5-tetraalkoxyphenylethynylbenzene (TPEB), and are excellent candidates for a variety of advanced materials applications, such as organic light-emitting diodes, solar cells and optical storage devices [9][10][11][12][13][14][15][16]. Carbon-rich cruciforms already possess demonstrated potential as nonlinear optical/two-photon absorption [17,18] and fluorescent sensing materials [19][20][21]. Changes in the substituents, substitution pattern, electronic structure and conjugation can provide highly variable photo physical properties for such materials.…”

Section: Introductionmentioning

confidence: 99%

Influence of Mesogenic Properties of Cruciform-Shaped Liquid Crystals by Incorporating Side-Arms with a Laterally-Substituted-Fluorine

et al. 2013

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Fluoro substitution in thermotropic liquid crystals provides a general way of modifying the properties of a parent system. Transition temperatures, mesophase types and other physical properties can be affected by fluoro substitution, so that frequently the behaviors of the parent compound can be manipulated and improved in a predictable manner. This paper discusses the effects of a fluoro substitution in each side-arm of 1,2,4,5-tetrakis((4-(alkoxy)phenyl)ethynyl)benzenes on the resulting mesomorphic properties characterized by optical polarizing microscopy and differential scanning calorimetry. Without any fluoro-substituted side-arms, longer chain-length leads to a wider nematic temperature range on cooling. Incorporation of a fluoro substitution in each side-arm induces the formation of a lamellar suprastructure, lowers transition temperatures and results in a wider mesophase temperature range on cooling.

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“…[54,61] Related structural motives were already investigated as electrooptically active chromophores in self-assembled thin films, [62,63] as chromophores with tuneable band gaps, [64] as metal ion [65][66][67] or pH [68] sensors, [69] and as building blocks of coordination polymers. [70] The proposed switching mechanism relies on the different electronic transparencies of the bar subunits and the interplay of their anchor groups with the electrochemical potential.…”

Section: Introductionmentioning

confidence: 99%

Oligoaryl Cruciform Structures as Model Compounds for Coordination‐Induced Single‐Molecule Switches

Grunder¹,

Huber²,

Wu³

et al. 2010

Eur J Org Chem

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The synthesis of two new cruciform structures 3 and 4 comprising an oligo(phenylene-vinylene) (OPV) and a perpendicular oligoaryl bar -namely an oligophenylene (OP) (3) and a naphthyl-phenyl-naphthyl system (4) -is reported. The OPV rod consists of two terminal pyridine units, whereas the oligoaryl rod bears two terminal acetylsulfanyl groups as protected anchor groups. The OPV bar was assembled via a Horner-Wadsworth-Emmons reaction, which directly led to the desired E,E isomers. The perpendicular oligoaryl bars were assembled with a Suzuki reaction using the corresponding boronic acids, which were already fitted with an ethyl-trimethylsilane (ethyl-TMS) sulfanyl group. In a last step, the ethyl-TMS-protected sulfur atoms were transpro-

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Self-Assembled Electrooptic Thin Films with Remarkably Blue-Shifted Optical Absorption Based on an X-Shaped Chromophore

Cited by 84 publications

References 29 publications

Theory-Guided Design of Organic Electro-Optic Materials and Devices

Theory-Guided Design of Organic Electro-Optic Materials and Devices

Influence of Mesogenic Properties of Cruciform-Shaped Liquid Crystals by Incorporating Side-Arms with a Laterally-Substituted-Fluorine

Oligoaryl Cruciform Structures as Model Compounds for Coordination‐Induced Single‐Molecule Switches

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