Synthesis of Triphenylamine-Cored Dendritic Two-Photon Absorbing Chromophores

Wei, Peng; Bi, Xiangdong; Wu, Zhe; Xu, Zhi

doi:10.1021/ol050905n

Cited by 111 publications

(51 citation statements)

References 41 publications

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“…Styrene and tert-butyl methacrylate (Aldrich) were distillated over CaH 2 under reduced pressure. 2,7-Bis(diethylphosphono)-9,9-dihexylfluorene (8) [18], compounds 5 [3b], 6 [3b], 7 [3b], 9 [19], and 11 [20] were prepared according to known procedures.…”

Section: Methodsmentioning

confidence: 99%

Hydrophobic Chromophores in Aqueous Micellar Solution Showing Large Two‐Photon Absorption Cross Sections

Tian

Chen

Cheng

et al. 2007

Adv Funct Materials

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A series of new hydrophobic two‐photon absorbing (2PA) chromophores with varied electron‐donating groups in quasi‐linear and multibranched structures are synthesized to correlate their structure/photophysical property relationships. The feasibility of using these large two‐photon absorption cross‐sectional (δ, expressed in GM = 1 × 10–50 cm4 s photon–1 molecule–1) materials in aqueous solution is also explored. All four hydrophobic 2PA materials can be encapsulated into micelles generated by dispersing an amphiphilic block copolymer, poly(methacrylic acid)‐block‐polystyrene (PMAA‐b‐PS), into water. The micellar nanostructures are characterized using dynamic light scattering, atomic force microscopy, and transmission electron microscopy. After these dyes are incorporated into micelles, they exhibit strong fluorescence in water. It is found that the quantum yield and δ values of these chromophores are strongly dependent on the diameters of the micelles, concentrations of the PMAA‐b‐PS, and molecular structures of the 2PA chromophores. One of the compounds that has a strong triarylamino donor and a multibranched structure exhibits a large δ value of 2790 GM and high quantum yield (0.56) in micelle‐containing water. Although this value is smaller than the original value of 5300 GM in toluene, it is still substantially larger than the values of most water‐soluble 2PA materials, which have δ values of less than 100 GM.

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Section: Methodsmentioning

confidence: 99%

Hydrophobic Chromophores in Aqueous Micellar Solution Showing Large Two‐Photon Absorption Cross Sections

Tian

Chen

Cheng

et al. 2007

Adv Funct Materials

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“…TPA-based oligomers with linear, dendrimer or star-shaped architectures have been synthesized and studied for various applications as organic light emitting materials or field-effect transistors and two-photon related applications [8][9][10][11][12][13][14][15][16][17] while TPA-based polymers have been studied due to their excellent hole-transporting capacity, low ionization potential, high quantum yield of photoluminescence and thermal stability [16][17][18][19][20][21][22][23][24][25][26]. All these properties are attributed to the presence of a TPA group.…”

Section: Introductionmentioning

confidence: 99%

Polyazomethines with Triphenylamine Groups Synthesized by Suzuki Polycondensation Reactions

Mihai

Ivanoiu

Vacareanu³

et al. 2012

Designed Monomers and Polymers

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Two new linear, conjugated triphenylamine-based polyazomethines were synthesized by the Suzuki polycondensation of N,N -bis[4-(4-bromophenyl)(phenyl)aminobenzylidene]-1,4-phenylendiamine with 2,5-thiophenediboronic acid and 9,9-dioctylfluorene-2,7-diboronic acid, respectively, using Pd(PPh 3 ) 4 as catalyst. The obtained structures were characterized by spectral methods ( 1 H-NMR, FT-IR, UV-Vis and fluorescence), as well as by thermal analysis.

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“…A triphenylamine core was chosen, which allowed the alignment of three trifluoroacetyl stilbene units. This skeletal structure was employed since triphenylamine is known for its structural rigidity, [17] facile convertibility, and strong fluorescence. [18] Furthermore, we replaced the three reactive trifluoroacetyl groups with one or two unreactive nitro functions to evaluate substitution effects on selectivity and sensitivity.…”

Section: Introductionmentioning

confidence: 99%

Star‐Shaped Tripodal Chemosensors for the Detection of Aliphatic Amines

Körsten

Mohr

2010

Chemistry A European J

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In this work, three new tripodal triphenylamine dyes are presented that are capable of reversibly binding amines and diamines to form hemiaminals through a covalent bond. The dyes were synthesized by the Heck reaction and possess stilbene units with one, two, or three trifluoroacetyl groups as receptor moieties. Their interaction with amines and diamines led to changes in their absorption and emission properties, which were detected by UV/Vis and fluorescence spectroscopy. The influence of the number of trifluoroacetyl receptor moieties on the selectivity and sensitivity of the dyes was studied. Enhanced sensitivity and selectivity for diaminoalkanes was found for the dye we have labeled Tripod-1, with three chemically reactive trifluoroacetyl groups, related to only one or two trifluoroacetyl groups in the dye molecule.

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Synthesis of Triphenylamine-Cored Dendritic Two-Photon Absorbing Chromophores

Cited by 111 publications

References 41 publications

Hydrophobic Chromophores in Aqueous Micellar Solution Showing Large Two‐Photon Absorption Cross Sections

Hydrophobic Chromophores in Aqueous Micellar Solution Showing Large Two‐Photon Absorption Cross Sections

Polyazomethines with Triphenylamine Groups Synthesized by Suzuki Polycondensation Reactions

Star‐Shaped Tripodal Chemosensors for the Detection of Aliphatic Amines

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