Triphenylamine-Cored Bifunctional Organic Molecules for Two-Photon Absorption and Photorefraction

Lee, Hye Jeong; Sohn, Jubee; Hwang, and Jaehoon; Park, Soo Young; and, Haeyoung Choi; Cha, Myoungsik

doi:10.1021/cm0343756

Cited by 192 publications

(99 citation statements)

References 44 publications

(41 reference statements)

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“…31 The TPEF experiments reported here provide experimental evidence that the TPA enhancement is strongly wavelengthdependent. The TPA enhancement also significantly increases close to the visible region ( Figure 11).…”

Section: Resultsmentioning

confidence: 57%

“…[1][2][3] More recently, quadrupolar systems have been designed and investigated [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] and have shown improved properties, in particular with respect to the trade-off between optical transparency and NLO performance. Lately, attention has turned toward multipolar [22][23][24][25][26][27][28][29][30][31][32][33] and branched structures including dendrimers. 23,24,28,[33][34][35][36][37][38][39][40][41][42][43] Given the huge synthetic effort needed to build such supramolecular structures, a detailed understanding of the effect of branching of molecular entities on the linear and nonlinear optical properties is of major interest.…”

Section: Introductionmentioning

confidence: 99%

“…Triphenylamine is a well-known electrondonating moiety, which has been used both in the design of octupoles for second-order NLO effects [58][59][60][61] and in branched and dendritic structures for molecular TPA. [23][24][25][29][30][31][32][36][37][38]41,42 In this paper, we first briefly describe the synthesis of the studied chromophores, as well as experimental and computational details (section 2). Linear absorption and fluorescence properties of the compounds are then thoroughly explored through a combined analysis of both experimental and theoretical results (section 3).…”

Section: Introductionmentioning

confidence: 99%

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Effects of (Multi)branching of Dipolar Chromophores on Photophysical Properties and Two-Photon Absorption

et al. 2005

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To investigate the effect of branching on linear and nonlinear optical properties, a specific series of chromophores, epitome of (multi)branched dipoles, has been thoroughly explored by a combined theoretical and experimental approach. Excited-state structure calculations based on quantum-chemical techniques (timedependent density functional theory) as well as a Frenkel exciton model nicely complement experimental photoluminescence and one-and two-photon absorption findings and contribute to their interpretation. This allowed us to get a deep insight into the nature of fundamental excited-state dynamics and the nonlinear optical (NLO) response involved. Both experiment and theory reveal that a multidimensional intramolecular charge transfer takes place from the donating moiety to the periphery of the branched molecules upon excitation, while fluorescence stems from an excited state localized on one of the dipolar branches. Branching is also observed to lead to cooperative enhancement of two-photon absorption (TPA) while maintaining high fluorescence quantum yield, thanks to localization of the emitting state. The comparison between results obtained in the Frenkel exciton scheme and ab initio results suggests the coherent coupling between branches as one of the possible mechanisms for the observed enhancement. New strategies for the rational design of NLO molecular assemblies are thus inferred on the basis of the acquired insights.

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Section: Resultsmentioning

confidence: 57%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effects of (Multi)branching of Dipolar Chromophores on Photophysical Properties and Two-Photon Absorption

et al. 2005

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Experimental details

Single-crystal X-ray diffraction data of the compound were collected on an ADSC Quantum210 detector at Beamline 4A MXW of Pohang Light Source.

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confidence: 99%

“…Source of material 4-Formylphenyl-diphenylamine was prepared by the VilsmeierHacck formylation of triphenylamine by the reported methods [1,2]. Well shaped yellowish crystal of the title compound was obtained by slow evaporation of its solution in hexane at room temperature.…”

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confidence: 99%

Crystal structure of 4-formylphenyl-diphenylamine, C19H15NO

Li¹,

Lim²,

Kim³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material 4-Formylphenyl-diphenylamine was prepared by the VilsmeierHacck formylation of triphenylamine by the reported methods [1,2]. Well shaped yellowish crystal of the title compound was obtained by slow evaporation of its solution in hexane at room temperature. Experimental detailsSingle-crystal X-ray diffraction data of the compound were collected on an ADSC Quantum210 detector at Beamline 4A MXW of Pohang Light Source. The crystals evaluation and data collections were done with adetector-to-crystal distance of 6.0 . cm. Preliminary cell parameters and an orientation matrix were determined from 36 sets of frames collected at scan intervals of 5°with an exposure time of 1second per frame. DiscussionIn the crystal structure of 4-formyltriphenylamine the mean plane of C16-C19-O1 is slightly twisted out of phenyl ring (C13-C18) with adihedral angle of 3.48(1)°.The conformation of the three phenyl rings (C1-C6, C7-C12, and C13-C18) is like the blades of ap ropeller (figure, top). Only one hydrogen bond was found formed between two enantiomers (C12-H10···O i ,s ymmetry code i: x,0.5-y,0.5+z)( figure, bottom). The head-to-head stacked molecules display usual slipped stacking geometry with no interacting p system and the centroid-centroid distance is 4.5536(8) Å and the angle between the ring normal and vectors between the ring centroids is 40.42(2)°.The shortest atom-atom contact between the two parallel planes is 3.551(2) Å (C16 to C16ii ,symmetry code ii: 2-x,-y,-z), characteristic of aweak interaction [3]. Less usual carbonyl···p interaction is observed in the molecular assembly: (figure, bottom). The carbonyl group is almost parallel to phenyl ring of the neighbour molecule, giving rise to the interaction of the p electron of carbonyl to the phenyl ring. The torsional angle C19-O1-centroid is 78.19(8)°,w hile the O1=C19···centroid angle is 82.13(8)°.The oxygen atom and the p system are separated by 3.581(1) Å,while carbon atom and the p system are separated by 3.539(2) Å.T he carbonyl is directly above the phenyl ring with the distance 3.5073(7) Å between the two centroid. Both oxygen and carbon atom take part in this interaction.Z. Kristallogr. NCS 224 (2009)

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Tris(4‐cyanophenyl)amine: Simple Synthesis via Self‐assembly; Strong Fluorescence in Solution, Nano/microcrystals, and Solid

Patra

Anthony

Radhakrishnan

2007

Adv Funct Materials

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The threefold symmetric molecule, tris(4‐cyanophenyl)amine (TCPA) is synthesized from 4‐fluorocyanobenzene by treatment with potassium carbonate in dimethylsulfoxide; the occurrence of the reaction without any amine reagent suggests the involvement of a novel self‐assembly process. A reprecipitation strategy provides stable colloids containing highly monodisperse nano/microcrystals with well‐defined cubic morphology and sizes tunable from 250 to 500 nm. The solution, colloid, and solid states of TCPA exhibit strong blue fluorescence; the colloid shows dual emission with an unusually small Stokes shift. Computational investigations are carried out on the molecule and supramolecular assemblies derived from the crystal structure. Coupled with detailed spectroscopic studies, they show that the emission in the colloidal and solid states can be attributed to energy levels resulting from the intermolecular interactions within different aggregation motifs in the condensed phase and energy cascades between them. The computations also reveal the presence of cooperative interactions in the molecular crystal contributing to its high thermal stability. The strong light emission exhibited by TCPA, concurrently in the solution, nano/microcrystal, and solid states establishes it as a novel molecular material of potential practical utility; it has led to the exploration of the underlying mechanism that describes the phenomena observed in the different physical states.

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Triphenylamine-Cored Bifunctional Organic Molecules for Two-Photon Absorption and Photorefraction

Cited by 192 publications

References 44 publications

Effects of (Multi)branching of Dipolar Chromophores on Photophysical Properties and Two-Photon Absorption

Effects of (Multi)branching of Dipolar Chromophores on Photophysical Properties and Two-Photon Absorption

Crystal structure of 4-formylphenyl-diphenylamine, C19H15NO

Tris(4‐cyanophenyl)amine: Simple Synthesis via Self‐assembly; Strong Fluorescence in Solution, Nano/microcrystals, and Solid

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