Synthesis and photoluminescent properties of conjugated aryl–vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives

Bosiak, Mariusz J.; Rakowiecki, Marcin; Orłowska, K; Kędziera, Dariusz; Adams, Jörg

doi:10.1016/j.dyepig.2013.07.006

Cited by 8 publications

(7 citation statements)

References 40 publications

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“…Water (50 mL) was added, and the crude product was extracted with DCM (3 × 50 mL), dried over anhydrous MgSO 4 , filtered through a short silica pad, dry-loaded to silica gel, and purified by a column chromatography using petroleum ether and DCM (2:1) as mobile phase to provide 0.65 g (39%) of 11 as a yellow solid. mp 162–163 °C (lit . mp 162–164 °C).…”

Section: Methodsmentioning

confidence: 99%

“…31 For this purpose, suitable 2,3,4,5-tetrafluoro derivatives 10, 12, and 14 were synthesized. Route B (Scheme 2) began with the synthesis of (2,3,4,5-tetrafluorobenzyl)triphenylphosphonium bromide (9) that can be reacted with benzo[c]phenanthrene-2-carbaldehyde 19 (8) or (E)-4-[2-(2naphthalenyl)ethenyl]benzaldehyde 51 (11) to corresponding tetrafluorinated stilbenes 10 or 12 in 71% and 74% yield, respectively. The reaction provided (E)-10 isomer and a mixture of (E,E)-and (E,Z)-12 isomers.…”

Section: Scheme 2 Synthetic Route Bmentioning

confidence: 99%

“…mp 162−163 °C (lit. 51 (12). A 500 mL round-bottomed flask was charged with dry THF (200 mL) and diisopropylamine (0.76 mL, 5.42 mmol, 1.4 equiv) under argon atmosphere.…”

Section: -Trifluoromethylsulfonyloxy-7-(2-phenylethenyl)n a P H T H A...mentioning

confidence: 99%

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Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings

Cı́rkva¹,

Jakubík²,

Strašák³

et al. 2019

J. Org. Chem.

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The first racemization-stable helicene derivatives fluorinated at terminal rings, 1,2,3,4-tetrafluoro[6]helicene (6) and 1,2,3,4,13,14,15,16-octafluoro[6]helicene (15), were synthesized via the Wittig reaction followed by oxidative photocyclization in an overall yield of 41% of 6 and 76% of 15. The changed electronic structure in fluorinated helicenes was reflected in a slight shift of UV–vis absorption, fluorescence excitation, and emission spectra maxima when compared to unsubstituted [6]helicene. Cyclic voltammetry revealed a moderate decrease in the HOMO–LUMO gap with increasing fluorination. The specific rotation of tetrafluoro[6]helicene 6 enantiomers was found to be approximately 25% lower than that of unsubstituted [6]helicene. The theoretical study of the racemization barrier suggested a reasonable shift toward higher energy with increasing fluorination. The increasing fluorination also significantly affected the intermolecular interactions in the crystal lattice. The observed CH···F interactions led to the formation of 1D-molecular chains in the crystal structures of both fluorinated helicenes.

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Section: Methodsmentioning

confidence: 99%

Section: Scheme 2 Synthetic Route Bmentioning

confidence: 99%

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Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings

Cı́rkva¹,

Jakubík²,

Strašák³

et al. 2019

J. Org. Chem.

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“…1) [22]. Derivatives integrating BDF units substituted on the furan positions often present high emission properties in the solid state that can be used for OLED applications [23][24][25][26][27][28]. BDF constitute also an attractive electron donor building block for the synthesis of donor -acceptor copolymers [29][30][31][32][33][34][35][36] or small molecules [37] used as donor materials in OPV.…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis and optical properties of extended TPA-Benzodifuran derivatives connected by cyano-vinylene junctions

2018

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Two new conjugated molecules based on triphenylaminebenzo [1,2-b:4,5-b']difuran moieties and integrating cyanovinyl bonds have been synthesized by using the new benzodifuran-acetonitrile synthon, easily and rapidly prepared in two steps from 2,2'-(2,5-dihydroxy-1,4-phenylene)diacetic acid. The electronic properties of the molecules were analysed by UV-Vis absorption and emission spectroscopies and cyclic voltammetry. The potential use of the molecules as donor materials for photovoltaic conversion were evaluated in simple bilayer solar cells using C60 as the acceptor materials. The comparison between the two derivatives reveals that the extension of the conjugated system with the insertion of furan cycles leads to a narrowing band gap, a better emission property, a direct access to dication state and an enhancement of the photovoltaic characteristics.

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“…[23][24][25][26][27][28] Recently, the research group of Mariusz Jan Bosiak showed the utility of benzofurans in photovoltaic and optoelectronic properties, wherein benzofurans absorb and emit the light. [29][30][31][32] While, one-pot synthesis of benzofurans, under homogeneous catalysis, is well established. Recently, the synthetic community turned their interest to develop new methods for the synthesis of benzofurans by means of heterogeneous catalytic conversion.…”

Section: Introductionmentioning

confidence: 99%

Recyclable Pd/CuFe₂O₄ nanowires: a highly active catalyst for C–C couplings and synthesis of benzofuran derivatives

et al. 2018

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Synthesis and photoluminescent properties of conjugated aryl–vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives

Cited by 8 publications

References 40 publications

Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings

Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings

Facile synthesis and optical properties of extended TPA-Benzodifuran derivatives connected by cyano-vinylene junctions

Recyclable Pd/CuFe₂O₄ nanowires: a highly active catalyst for C–C couplings and synthesis of benzofuran derivatives

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Synthesis and photoluminescent properties of conjugated aryl–vinyl dioctyl 2,6-dimethylbenzofuro[5,6-b]furan-3,7-dicarboxylate derivatives

Cited by 8 publications

References 40 publications

Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings

Preparation and Physicochemical Properties of [6]Helicenes Fluorinated at Terminal Rings

Facile synthesis and optical properties of extended TPA-Benzodifuran derivatives connected by cyano-vinylene junctions

Recyclable Pd/CuFe2O4 nanowires: a highly active catalyst for C–C couplings and synthesis of benzofuran derivatives

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Recyclable Pd/CuFe₂O₄ nanowires: a highly active catalyst for C–C couplings and synthesis of benzofuran derivatives