Untersuchungen über Stilbene, XLII. [4‐Vinyl‐styryil]‐Aromaten

Drefahl, Günther; Plötner, Gerhard; Winnefeld, K

doi:10.1002/cber.19610940811

Cited by 9 publications

(7 citation statements)

References 4 publications

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“…For preparation of monomer 4‐(2‐(9‐anthryl))‐vinyl‐styrene (AVS), witting reaction38 was performed between the (4‐vinylbenzyl)triphenylphosphonium chloride and 9‐anthraldehyde. Thus we obtained the desired monomer in gram‐scale quantities, which was fully characterized using 1 H NMR spectroscopy, Figure 5.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of AB‐type block copolymers containing benzoxazole and anthracene groups by ATRP and fluorescent property

Yuan

et al. 2007

J. Polym. Sci. A Polym. Chem.

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Two functional monomers, methacrylic acid 4‐(2‐benzoxazol)‐benzyl ester (MABE) containing the benzoxazole group and 4‐(2‐(9‐anthryl))‐vinyl‐styrene (AVS) containing the anthracene group were synthesized by rational design. The MABE was polymerized via atom transfer radical polymerization (ATRP) using ethyl 2‐bromoisobutyrate (EBIB) as initiator in CuBr/N,N,N′,N″,N″‐pentamethyldiethylenetriamine (PMDETA) catalyst system; block copolymers poly(MABE‐b‐AVS) was obtained, which was conducted by using poly(MABE) as macro‐initiator, AVS as the second monomer, and CuBr/PMDETA as catalyst. The constitute of two monomers in block copolymers poly(MABE‐b‐AVS) by ATRP could be adjusted, that is the constitute of the benzoxazole group and the anthracene group could be controlled in AB‐type block copolymers. Moreover, the fluorescent properties of homopolymers poly(MABE) and block copolymers poly(MABE‐b‐AVS) were discussed herein. With the excitation at λex = 330 nm, the fluorescent emission spectrum of poly(MABE) solution showed emission at 375 nm corresponding to the benzoxazole‐based part; with the same excitation, the fluorescent emission spectrum of poly(MABE‐b‐AVS) solution showed a broad peek at 330–600 nm when the monomer AVS to the total monomers mole ratio was 0.31, and the fluorescent emission spectrum of poly(MABE‐b‐AVS) in film state only showed one peak at 525 nm corresponding to the anthracene‐based unit that indicated a complete energy transfer from the benzoxazole group to the anthracene group. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 3894–3901, 2007

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Section: Resultsmentioning

confidence: 99%

Synthesis of AB‐type block copolymers containing benzoxazole and anthracene groups by ATRP and fluorescent property

Yuan

et al. 2007

J. Polym. Sci. A Polym. Chem.

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“…All chemicals were purchased from J&K Scientific and used as received without further purification. 1-Diethoxyphosphorylmethyl-2-(9-anthryl)vinylbenzene, 1-diethoxyphosphorylmethyl-3-(9-anthryl)vinylbenzene, 1-diethoxyphosphorylmethyl-4-(9-anthryl)vinylbenzene, and 4-[(9-anthryl)vinyl]benzyltriphenylphosphonium bromide were prepared according to the published procedures. ,, …”

Section: Methodsmentioning

confidence: 99%

“…1-Diethoxyphosphorylmethyl-2-(9anthryl)vinylbenzene, 1-diethoxyphosphorylmethyl-3-(9anthryl)vinylbenzene, 1-diethoxyphosphorylmethyl-4-(9anthryl)vinylbenzene, and 4-[(9-anthryl)vinyl]benzyltriphenylphosphonium bromide were prepared according to the published procedures. 18,42,43 1 H and 13 C NMR spectra were recorded on a Bruker Avance 400 spectrometer. Elemental analyses were performed using a PerkinElmer 2400II elemental analyzer.…”

Section: ■ Conclusionmentioning

confidence: 99%

Substitution Position and Vinylene Bond Geometry Modulating the Fluorescence Solvatochromism and Aggregation-Induced Emission of (9-Anthryl)vinyl(1-pyrenyl)vinylbenzene Isomers

Yang

Miao

et al. 2016

J. Phys. Chem. C

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Computational detail. All calculations were carried out with the program package Gaussian 09. The ground-state (S 0) geometry was optimized in the gas phase by density functional theory (DFT) at the CAM-B3LYP/6-31G level. Using the optimized ground-state geometry as starting coordinates, the first excited-state (S 1) geometry was optimized using time-dependent density functional theory (TD-DFT) at the CAM-B3LYP/6-31G level. No symmetry constraint was used during the geometry optimization. Frequency calculations were performed on all minima to check the absence of negative frequencies. Dipole moment in the S 1 state was determined using "density" keyword. S2

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“…All chemicals were purchased from J&K Scientific and used as received without further purification. 4-[(9-Anthryl)vinyl]benzyltriphenylphosphonium bromide, 1-dimethoxyphosphorylmethyl-3-(9-anthryl)vinylbenzene, and 1-dimethoxyphosphorylmethyl-2-(9-anthryl)vinylbenzene were prepared according to the published procedures. , …”

Section: Methodsmentioning

confidence: 99%

“…4 -[ ( 9 -A n t h r y l ) v i n y l ]benzyltriphenylphosphonium bromide, 1-dimethoxyphosphorylmethyl-3-(9-anthryl)vinylbenzene, and 1-dimethoxyphosphorylmethyl-2-(9-anthryl)vinylbenzene were prepared according to the published procedures. 37,47 1 H and 13 C NMR spectra were recorded on a Bruker Avance 400 spectrometer. High-resolution mass spectral analyses were carried out on a Bruker maXis UHR-TOF mass spectrometer.…”

Section: ■ Conclusionmentioning

confidence: 99%

(9-Anthryl)vinyl(9-phenanthryl)vinylbenzene Position Isomers: Intriguing Effects of Molecular Configuration on Polymorphism, Solvatochromism, and Aggregation-Induced Emission Properties

Qiu

Miao

et al. 2015

J. Phys. Chem. C

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Three [(9-anthryl)vinyl][(9-phenanthryl)vinyl]benzene (APB) position isomers were synthesized and compared. The molecular configuration exhibits an extraordinary ability to affect polymorphism probability, unexpected solvatochromism, and aggregation-induced emission property. With the substitution changing from para-, ortho-, to meta-position, the polymorph number changes from 1, 2, to 3. Both 1,2-APB and 1,3-APB display a temperature-induced crystal-to-crystal phase transition. Furthermore, a pair of concomitant conformational polymorphs were obtained for 1,3-APB. Crystal structure analyses reveal that the steric hindrance between the two substituents leads to different molecular conformation and packing pattern. The unexpected solvatochromism is attributed to the strong electron-withdrawing ability of anthracene against phenanthrene, which produces permanent dipole moment. The solvatochromic degree is determined by the conjugative effect which varies with substitution position. 1,4-APB displays the most remarkable solvatochromic effect. Furthermore, it shows a totally different emission decay dynamics from 1,2-APB and 1,3-APB in polar solvents. Interestingly, the solution fluorescence quantum yields of these three isomers all increase with increased solvent polarity, displaying a negative solvatokinetic effect. Both 1,2-APB and 1,4-APB display an aggregation-induced emission enhancement. Though 1,3-APB is quenched in the solid state, it emits most efficiently amongst these three isomers either in solution or in solid state. The effect of the medium environment on the radiative process plays a vital role in determining their different aggregation-induced emission behaviours.

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Untersuchungen über Stilbene, XLII. [4‐Vinyl‐styryil]‐Aromaten

Cited by 9 publications

References 4 publications

Synthesis of AB‐type block copolymers containing benzoxazole and anthracene groups by ATRP and fluorescent property

Synthesis of AB‐type block copolymers containing benzoxazole and anthracene groups by ATRP and fluorescent property

Substitution Position and Vinylene Bond Geometry Modulating the Fluorescence Solvatochromism and Aggregation-Induced Emission of (9-Anthryl)vinyl(1-pyrenyl)vinylbenzene Isomers

(9-Anthryl)vinyl(9-phenanthryl)vinylbenzene Position Isomers: Intriguing Effects of Molecular Configuration on Polymorphism, Solvatochromism, and Aggregation-Induced Emission Properties

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