Synthesis and photophysical properties of new two-photon absorption chromophores containing a diacetylene moiety as the central π-bridge

Iwase, Yoichiro; Kamada, Kei; Ohta, Koji; Kondo, Koichi

doi:10.1039/b211268j

Cited by 96 publications

(64 citation statements)

References 43 publications

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“…In the quest of improving NLO properties, attention has been essentially focused on dipolar molecules for several decades. [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.…”

Section: Introductionmentioning

confidence: 99%

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: Introductionmentioning

confidence: 99%

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

et al. 2005

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“…Usually double bonds, due to their simple synthetic accessibility, are used in the backbone of the PIs to extend the conjugation length although the so obtained r TPA is normally lower than that of the triple-bondcontaining counterparts. 19,20 However, double bonds tend to attenuate the desired photochemical processes by cis-trans isomerization.…”

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confidence: 99%

Synthesis and structure‐activity relationship of several aromatic ketone‐based two‐photon initiators

Siklos

Pucher

et al. 2011

J. Polym. Sci. A Polym. Chem.

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Several novel aromatic ketone-based two-photon initiators containing triple bonds and dialkylamino groups were synthesized and the structure-activity relationships were evaluated. Branched alkyl chains were used at the terminal donor groups to improve the solubility in the multifunctional monomers. Because of the long conjugation length and good coplanarity, the evaluated initiators showed large two-photon cross section values, while their fluorescence lifetimes and quantum yields strongly depend on the solvent polarity. All novel initiators exhibited high activity in terms of two-photon-induced microfabrication. This is especially true for fluorenone-based derivatives, which displayed much broader processing windows than well-known highly active initiators from the literature and commercially available initiators. While the new photoinitiators gave high reactivity in two-photoninduced photopolymerization at concentration as low as 0.1% wt, these compounds are surprisingly stable under one photon condition and nearly no photo initiation activity was found in classical photo DSC experiment.

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“…In comparison to the phosphonate (2), the phospholipid phosphatide (3) possesses the advantages of low stereo-hindrance effect and high flexibility [13], which increased its reaction ability with aldehyde groups. The results indicated that the obtained average molecular weight by Wittig-Horner reaction was greatly improved (from M n =2087 in Wittig reaction to M n =10690 in Wittig-Horner reaction).…”

Section: Resultsmentioning

confidence: 99%

The Preparation and Fluorescence of Conjugated Polymer Nanoparticles with Triphenylamine Derivatives

Zhu¹,

Zhang²,

Qin³

et al. 2014

Proceedings of the 2015 International Conference on Material Science and Applications

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Abstract. The conjugated polymers TEB1 and TEB2 were synthesized by Wittig and Wittig-Horner reaction, and the conjugated polymer nanoparticles CPNs1 and CPNs2 were prepared by reprecipitation method with TEB1 and TEB2, respectively. Moreover, the morphology and fluorescence of CPNs were investigated. The synthetic results indicated that the average molecular weight was improved effectively by Wittig-Horner reaction. CPNs2 with a higher average molecular weight showed a better feature and bright fluorescence.

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Synthesis and photophysical properties of new two-photon absorption chromophores containing a diacetylene moiety as the central π-bridge

Cited by 96 publications

References 43 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

Synthesis and structure‐activity relationship of several aromatic ketone‐based two‐photon initiators

The Preparation and Fluorescence of Conjugated Polymer Nanoparticles with Triphenylamine Derivatives

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