Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption

Lartia, Rémy; Allain, Clémence; Bordeau, Guillaume; Schmidt, Falk; Fiorini–Debuisschert, Céline; Charra, Fabrice; Teulade-Fichou, Marie-Paule

doi:10.1021/jo702002y

Cited by 130 publications

(72 citation statements)

References 66 publications

(147 reference statements)

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“…In this process, the ICT plays an important role in lowering the energy gap. [42][43][44][45] The quantum yields (Φ = 0.41 to Φ = 0.57) of the compounds 2 show higher than compound 1 (Φ = 0.01) with the electron-donating ability of the functional group para to the benzene. We also find that there are slight differences, in this process, this was thought to be the ICT plays an important role in lowering the energy gap.…”

Section: Photo-physical Propertiesmentioning

confidence: 96%

D-π-D chromophores based on dithieno[3,2-b:2',3'-d]thiophene (DTT): Potential application in the fabrication of solar cell

Wang

Akther

et al. 2017

Tetrahedron

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Section: Photo-physical Propertiesmentioning

confidence: 96%

D-π-D chromophores based on dithieno[3,2-b:2',3'-d]thiophene (DTT): Potential application in the fabrication of solar cell

Wang

Akther

et al. 2017

Tetrahedron

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“…And some papers have reported it as an excellent organic functional materials extensively [1,2]. In the title crystal structure the phenyl ring C13-C18 is planar.…”

Section: Discussionmentioning

confidence: 98%

Crystal structure of 2-(4-(diphenylamino)benzylidene)malononitrile, C22H15N3

Li¹,

Lim²,

Kim³

et al. 2009

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of material 2-(4-(Diphenylamino)benzylidene)malononitrile was prepared through the Knoevenagel condensation of 4-formyltriphenylamine and malononitrile. Chemicals used for the synthesis were commercially available, were of AR grade, and were used as received without further purification. Amixture of the trilphenylamine (273 mg, 1mmmol) and malononitrile (73 mg, 1.1 mmol) was dissolved in n-butanol 15mL. The mixture was stirred and heated to reflux. After 4h,the mixture was cooled down to room temperature. After the solvent was evaporated, the residual was purified by chromatography (CH 2 Cl 2 /hexane, 2:1) to yield cyanovinylene 305 mg (90 %) as an orange solid. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of its solution in hexane at room temperature. Experimental detailsSingle crystal X-ray diffraction data of the compound was collected on an ADSC Quantum210 detector at Beamline 4A MXW of Pohang Light Source. DiscussionThe title compound was synthesized as asolid fluorescence material. And some papers have reported it as an excellent organic functional materials extensively [1,2]. In the title crystal structure the phenyl ring C13-C18 is planar. The two −C≡Ng roups are in another plane ( figure, top). The mean plane of two C≡Ngroups bonded to C20 is slightly twisted out of the phenyl ring C13-C18 making ad ihedral angle of 9.50(6)°.The packing of molecules in the unit cell shows avery interesting pattern. The conformation of the three phenyl rings C1-C6, C7-C12, and C13-C18 connected to N1 is like the blades of apropeller making N1 achiral center and the dihedral angles between the three phenyl rings are 70.05(1)°,7 2.667(3)°,a nd 74.16(3)°,respectively. Four molecules including two left-hand and two right-hand spirals connected together head-to-tail in unit cell making the whole structure achiral. Molecules do not form intra-or inter-molecular hydrogen bonds. Other less unusual interactions, are p C=C···p and pN≡C···p interactions (figure, bottom). Because C19−H15···p interactions are observed every second layer, the distance between adjacent layers is different. The distance are 3.169 Å and 3.644 Å,respectively. Between any two layers, double bond (C19=C20) and triple bond (C22≡N2) interact with the phenyl ring C13-18 except C21≡N3.

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“…As an example, 3D ordering of fluorescent dyes through their spontaneous interactions with double stranded DNA can be taken into profit for efficient noncovalent DNA labelling [57]. A series of vinyl−pyridinium triphenylamines (TP−Py) derivatives was recently proposed and evaluated for its one− and two−photon absorption (2PA) induced−fluorescence pro− perties under biological conditions [58,59]. Interestingly, these compounds exhibit large stokes shifts resulting in red to far red emission.…”

Section: D Self-assembly Of Fluorescent Dyes On Dnamentioning

confidence: 99%

Self-assembly: mastering photonic processes at nanoscale

Fiorini

Charra

2010

Opto-Electronics Review

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Supramolecular ordering happens as an important parameter for the control of light emission processes. In this review paper, we discuss several examples of application of self-assembly to the realization of nano-structures designed in view of mastering specific photonic processes. This comprises the formation of highly localized plasmon modes in self-organized 2D assemblies of metal nanoparticles, the immobilization of dyes inside highly homogeneous 2D alveolar self-assembled molecular matrices and molecular 3D building blocks designed to combine in-plane periodicity and off-plane π-conjugated protrusions. Finally, we will discuss 3D self-assembly in solution with the example of fluorescent labelling of DNA.

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Synthetic Strategies to Derivatizable Triphenylamines Displaying High Two-Photon Absorption

Cited by 130 publications

References 66 publications

D-π-D chromophores based on dithieno[3,2-b:2',3'-d]thiophene (DTT): Potential application in the fabrication of solar cell

D-π-D chromophores based on dithieno[3,2-b:2',3'-d]thiophene (DTT): Potential application in the fabrication of solar cell

Crystal structure of 2-(4-(diphenylamino)benzylidene)malononitrile, C22H15N3

Self-assembly: mastering photonic processes at nanoscale

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