Synthesis of π-Conjugated Two Generation Dendrimer Composed of <i>p</i>-Phenylenevinylene Dendron and Triphenylamine Surface Group

Mizusaki, Masanobu; Yamada, Yuichiro; Obara, Satoru; Tada, Kentaro

doi:10.1246/cl.2012.516

Cited by 5 publications

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“…We have chosen oligo( p -phenyleneethnylene)s (OPE) − hydrocarbons as the π-conjugated core skeleton because of the flexibility in their synthetic strategies, though the system seems to have a disadvantage for the creation of fluorophore compared with OPV − hydrocarbons as shown in Figure , assuming that the Stokes shifts of OPV and OPE are almost close to each other. After some synthetic trials, we succeeded in the creation of the desired WRF using OPE as the π-conjugated core skeleton, which is described herein.…”

Section: Introductionmentioning

confidence: 99%

Highly Emissive Whole Rainbow Fluorophores Consisting of 1,4-Bis(2-phenylethynyl)benzene Core Skeleton: Design, Synthesis, and Light-Emitting Characteristics

et al. 2015

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To create the whole-rainbow-fluorophores (WRF) having the small Δλem (the difference of λem between a given fluorophore and nearest neighboring fluorophore having the same core skeleton) values (<20 nm) in full visible region (λem: 400-650 nm), the high log ε (>4.5), and the high Φf (>0.6), we investigated molecular design, synthesis, and light-emitting characteristics of the π-conjugated molecules (D/A-BPBs) consisting of 1,4-bis(phenylethynyl)benzene (BPB) modified by donor groups (OMe, SMe, NMe2, and NPh2) and an acceptor group (CN). As a result, synthesized 20 D/A-BPBs (1a-5d) were found to be the desired WRF. To get the intense red fluorophore (Φf> 0.7, λem > 610 nm), we synthesized new compounds (5e-5i) and elucidated their photophysical properties in CHCl3 solution. As a result, 5h, in which a 4-cyanophenyl group is introduced to the para-position of two benzene rings in the terminal NPh2 group of 5d, was found to be the desired intense red fluorophore (log ε = 4.56, Φf = 0.76, λem = 611 nm). The intramolecular charge-transfer nature of the S1 state of WRF (1a-5d) was elucidated by the positive linear relationship between optical transition energy (νem) from the S1 state to the S0 state and HOMO(D)-LUMO(A) difference, and the molecular orbitals calculated with the DFT method. It is demonstrated that our concept (Φf = 1/(exp(-Aπ) + 1)) connected with the relationship between Φf and magnitude (Aπ) of π conjugation length in the S1 state can be applied to WRF (1a-5d). It is suggested that the prediction of Φf from a structural model can be achieved by the equation Φf = 1/(exp(-((ν̃a - ν̃f)(1/2) × a(3/2)) + 1), where ν̃a and ν̃f are the wavenumber (cm(-1)) of absorption and fluorescence peaks, respectively, and a is the calculated molecular radius. From the viewpoint of application of WRF to various functional materials, the light-emitting characteristics of 1a-5i in doped polymer films were examined. It was demonstrated that 1a-5i dispersed in two kinds of polymer film (PST and PMMA) emit light at the whole visible region and have the small Δλem values (<20 nm) and the high Φf values (>0.6). Therefore, the present D/A-BPBs can be said to be the desired WRF even in the doped polymer film.

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Section: Introductionmentioning

confidence: 99%

Highly Emissive Whole Rainbow Fluorophores Consisting of 1,4-Bis(2-phenylethynyl)benzene Core Skeleton: Design, Synthesis, and Light-Emitting Characteristics

et al. 2015

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“…37 Polyphenylene (PP) dendrimer is a rigid π-conjugated dendrimer consisting of benzene rings 38 and has sufficient stability under the above reaction conditions. Phenylenevinylene dendrimers 39,40 have a similar structure and were also considered as a candidate to cover DPA, but it was not stable under the KMnO 4 oxidation process. Therefore, PP dendrimer was chosen as a shell to cover DPA, and the dendrimer was designed to have in total 4 times (DPA + PP) branching to form a jacket (Chart 1).…”

Section: Resultsmentioning

confidence: 99%

Poly-phenylene jacketed tailor-made dendritic phenylazomethine ligand for nanoparticle synthesis

et al. 2022

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Design, synthesis and characterization of triphenylamine-based conjugated porous polymers as fluorescent receptors for nitroaromatic derivatives

Vacareanu,

Bejan,

Bejan

et al. 2025

Dyes and Pigments

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Synthesis of π-Conjugated Two Generation Dendrimer Composed of p-Phenylenevinylene Dendron and Triphenylamine Surface Group

Abstract: π-Conjugated two generation dendrimer composed of p-phenylenevinylene dendron and triphenylamine surface group was synthesized via a convergent route. The dendrimer shows high solubility in organic solvents and fluorescence emission resulting from the p-phenylenevinylene site.

Cited by 5 publications

References 6 publications

Highly Emissive Whole Rainbow Fluorophores Consisting of 1,4-Bis(2-phenylethynyl)benzene Core Skeleton: Design, Synthesis, and Light-Emitting Characteristics

Highly Emissive Whole Rainbow Fluorophores Consisting of 1,4-Bis(2-phenylethynyl)benzene Core Skeleton: Design, Synthesis, and Light-Emitting Characteristics

Poly-phenylene jacketed tailor-made dendritic phenylazomethine ligand for nanoparticle synthesis

Design, synthesis and characterization of triphenylamine-based conjugated porous polymers as fluorescent receptors for nitroaromatic derivatives

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