New class of imidazoles incorporated with thiophenevinyl conjugation pathway for robust nonlinear optical chromophores

Santos, Javier; Mintz, Eric A.; Zehnder, Oliver; Bosshard, Christian; Bu, Xiu R.; Günter, Peter

doi:10.1016/s0040-4039(00)02143-2

Cited by 89 publications

(43 citation statements)

References 5 publications

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“…[12] ), Figure 1] are known to show intense blue emission with high quantum yields. Triaryl-substituted imidazoles are an interesting building block not only because of their unique linear and non-linear [13,14] optical properties but also because of their chemical characteristics in acid-base or metal-complexation reactions. [15][16][17] Materials based on imidazole also play an important role in ionic liquids [18,19] and in bio-systems like cytochrome c oxidase and their model compounds.…”

Section: Full Papermentioning

confidence: 99%

“…The solvent was removed under reduced pressure and the product was purified by column chromatography (2 vol.-% ethyl acetate in hexane) to provide 8.03 g (80%) of the title product as a yellow oil. 4,4 00 -Dichloro-2(,5(-bis(4,5-bis(4-octylphenyl)imidazol-2-yl)-(1,1(,4(,1 00 )terphenyl (14) Benzil 11 (4.03 g, 9.28 mmol), 4,4 00 -dichloro-(1,1 0 ,4 0 ,1 00 )terphenyl-2 0 , 5 0 -dicarbaldehyde (10) (1.5 g, 4.22 mmol), ammonium acetate (4.6 g, 59 mmol), and concentrated acetic acid (110 mL) were heated at 120 8C for 18 h under argon. After the reaction was cooled down, water (20 mL) was added and the mixture was made basic with aqueous ammonia.…”

Section: Experimental Partmentioning

confidence: 99%

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Blue Emission of a Soluble Poly(p‐phenylene) with a Cross‐Conjugated Bisimidazole‐Based Chromophore

Dierschke

Müllen

2007

Macro Chemistry & Physics

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A novel poly(p‐phenylene) (6) has been synthesized by a cruciform combination of a polyphenylene backbone with 2,2′‐(p‐phenylene)‐bis(4,5‐diphenylimidazole) (5) as an additional, orthogonal chromophore. Polymer 6 showed in solution and in the solid state, a blue‐green emission, which is obviously arising from the second bisimidazole‐based chromophore. UV‐Vis spectroscopy, and cyclic voltammetry revealed that the optical and electronic properties of 6 were fully determined by the incorporated 2,2′‐(1,4‐phenylene)bisimidazole structure. The bisimidazole unit led to high solubility and, despite the steric demand of the substituents, at the same time to the blue‐green emission of the poly(p‐phenylene) (6). In addition, the oxidation of 6 with potassium ferricyanide yielded a low bandgap polymer with a quinoid‐type structure and a bandgap of 1.6 eV.magnified image

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Section: Full Papermentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 99%

Blue Emission of a Soluble Poly(p‐phenylene) with a Cross‐Conjugated Bisimidazole‐Based Chromophore

Dierschke

Müllen

2007

Macro Chemistry & Physics

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“…[1][2][3] The chemical flexibility of this class of compounds allows the preparation of a large variety of related structures and, consequently, the tailoring of the chemiluminescent, [4] photochromic, [5,6] redox, [7] temperature-dependent UV-Vis absorbance, [8] and biological properties. [9][10][11] The chemiluminescence of 2,4,5-triphenylimidazole was first reported by Radziszewski in 1877, [12] who found that this compound emitted a yellow light when it reacted with oxygen in the presence of strong base.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and RAFT polymerization of a novel vinyl monomer containing both triarylimidazole and triazole moieties

Huang

Peng

Chen

et al. 2014

Designed Monomers and Polymers

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A novel monomer consisting of a 4-vinyl-1,2,3-triazole unit directly linked to a triphenylimidazole unit, 1-(4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl)-4-vinyl-1H-1,2,3-triazole (DVT), has been successfully synthesized using click chemistry followed by elimination reaction. Subsequently, poly(DVT) was prepared by the reversible addition-fragmentation chain transfer (RAFT) polymerization of DVT in dimethyl sulfoxide using S-dodecyl-S′-(α,α′-dimethyl-α″-acetic acid)-trithiocarbonate (DMP) as the RAFT agent and 2,2′-azobis(isobutyronitrile) (AIBN) as the initiator. Kinetic studies demonstrated that the polymerization process of DVT followed pseudo-first-order kinetics with respect to the monomer concentrations. The molecular weight of the resulting polymer increased linearly with monomer conversion, while a low polydispersity was maintained throughout. In addition, the poly(DVT) showed the characteristic of temperature-dependent absorbance in the near-ultraviolet (UV) spectral region, of which a linear dependence of UV absorbance on temperature was confirmed for the polymer both in solution and in solid states.

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“…It was mainly used to synthesize imidazole derivatives from 1,2-diketone and appropriate aldehydes [1][2][3][4][5][6][7][8][9][10][11]. The first is Radziszewski's classic synthesis from benzil(1,2-diphenylethane-1,2-dione), benzaldehyde and ammonia in 1882 [12].…”

Section: Introductionmentioning

confidence: 99%

Research on the reaction of furil with ammonium acetate

Wang

Chen

et al. 2011

Eur. J. Chem.

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KEYWORDSThe direct reaction of furil with ammonium acetate in refluxing glacial acetic acid under the absence of appropriate aldehydes was systematically studied. The principal product with furan rings and imidazole ring 2,4,5-tri(furan-2-yl)-1H-imidazole (I) was obtained in moderate yield, and two new byproducts containing furan rings were successfully purified by C18 reversed phase column. All compounds were characterized by elemental analysis, MS, IR, 1 H and 13 C NMR spectroscopy. The structure of I was further confirmed by the 13 C-1 H COSY spectroscopy. The putative reaction mechanism via stable 1,2-di(furan-2-yl)ethane-1,2-diimine, furan-2-yl-(2,4,5-tri-furan-2-yl-2H-imidazol-2-yl)-methanone and intermediate 5 traced by GC-MS was proposed.

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New class of imidazoles incorporated with thiophenevinyl conjugation pathway for robust nonlinear optical chromophores

Cited by 89 publications

References 5 publications

Blue Emission of a Soluble Poly(p‐phenylene) with a Cross‐Conjugated Bisimidazole‐Based Chromophore

Blue Emission of a Soluble Poly(p‐phenylene) with a Cross‐Conjugated Bisimidazole‐Based Chromophore

Synthesis and RAFT polymerization of a novel vinyl monomer containing both triarylimidazole and triazole moieties

Research on the reaction of furil with ammonium acetate

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