New anthracene‐containing phenylene‐ or thienylene‐vinylene copolymers: Synthesis, characterization, photophysics, and photovoltaics

Vellis, Panagiotis D.; Mikroyannidis, John A.; Bagnis, Diego; Valentini, Luca; Kenny, J. M.

doi:10.1002/app.29967

Cited by 6 publications

(8 citation statements)

References 49 publications

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“…As shown in Scheme , three anthracene-BODIPY dyads 2a , 2b , and 6 were first prepared and then submitted to an FeCl 3 -mediated oxidative cyclodehydrogenation reaction to generate fused π-systems. The anthracene monoaldehyde 1a (R = H) and 1b (R = Br) condensed with 2-ethylpyrrole in the presence of trifluoroacetic acid (TFA) followed by oxidative dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and complexation with BF 3 ·Et 2 O to give the corresponding anthracene–BODIPY dyads 2a and 2b in 31% and 23% yield, respectively. However, treatment of 2a or 2b with excessive anhydrous FeCl 3 in nitromethane and dichloromethane (DCM) did not afford the target products 3a or 3b .…”

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confidence: 99%

Anthracene-Fused BODIPYs as Near-Infrared Dyes with High Photostability

et al. 2011

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An anthracene unit was successfully fused to the zigzag edge of a boron dipyrromethene (BODIPY) core by an FeCl(3)-mediated oxidative cyclodehydrogenation reaction. Meanwhile, a dimer was also formed by both intramolecular cyclization and intermolecular coupling. The anthracene-fused BODIPY monomer 7a and dimer 7b showed small energy gaps (∼1.4 eV) and near-infrared absorption/emission. Moreover, they exhibited high photostability.

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confidence: 99%

Anthracene-Fused BODIPYs as Near-Infrared Dyes with High Photostability

et al. 2011

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“…9,10‐Dibromoanthracene ( 1 ) was purchased from Sigma Aldrich. The synthesis of 2 , 3 , 4 , 5 , 7 , 8 , 9 , and P1 was performed according to the descriptions in literature.…”

Section: Methodsmentioning

confidence: 99%

“…10-Bromoanthracene-9-carbaldehyde (5) 26 A solution of bromine (3.87 g, 24.24 mmol) in dichloromethane (10 mL) was added dropwise to a stirred solution of 9-formylanthracene (5 g, 24.24 mmol) in dichloromethane (150 mL) at room temperature. The mixture was refluxed for 4 h. After cooling down, the precipitate was filtered off to give a yellow-green solid.…”

Section: Monomer Synthesismentioning

confidence: 99%

“…8 Various types of synthetic operations were involved such as bromination, Williamson etherification, formylation, Sonogashira cross-coupling, trimethylsilyl-cleavage as well as bromomethylation and the Arbuzov reaction. The synthesis of the anthracene derivatives 5, 26 7, 11 and 9 27 used adjusted recipes. Detailed reaction schemes can be found in Supporting Information (Supporting Information Schemes S1 and S2).…”

Section: Synthesismentioning

confidence: 99%

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Polymers with alternating anthracene and phenylene building blocks linked by ethynylene and/or vinylene units: Studying structure‐properties‐relationships

Boudiba

Růžička

Ulbricht

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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Four conjugated polymers (P1-P4) consisting of alternating anthracene-9,10-diyl and 1,4-phenylene building blocks connected via ethynylene as well as vinylene (P1 and P2), ethynylene-only (P3), and vinylene-only (P4) moieties, respectively, were synthesized and studied. The phenylene units in all four polymers bear 2-ethylhexyloxy side-chains to promote good solubility. The three polymers with vinylene units (P1, P2, and P4) were prepared using the Horner-Wadsworth-Emmons reaction. For the synthesis of the aryleneethynylene polymer P3, the palladium-catalyzed Sonogashira cross-coupling reaction was used. The polymers were characterized by NMR, Fourier transform infrared spectroscopy, and Raman spectroscopy. Photophysical, absorption and photoluminescence, and electrochemical properties were studied. Spectroscopic ellipsometry measurements were performed to gain more insight on the optical properties. In addition, the transport properties were investigated using admittance spectroscopy. The bulk hole mobility and its dependence on the electric field were evaluated for P1 and P2.

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“…15 A variety of anthracene-containing copolymers and small molecules have recently been used for PV applications. [16][17][18][19][20][21] Very recently, we have synthesized an alternating phenylenevinylene copolymer with 2,5-bisazopyrrole segments along the backbone and the corresponding BF 2 -azopyrrole complex. The latter has been used as an n-type organic semiconductor for BHJ solar cells with a PCE of up to 2.32%.…”

Section: Introductionmentioning

confidence: 99%

Bulk Heterojunction Photovoltaics Using Broadly Absorbing Small Molecules Based on 2-Styryl-5-phenylazo-pyrrole

et al. 2010

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Three new soluble small molecules (B, B6, and A) with a low band gap based on 2-styryl-5-phenylazo-pyrrole were synthesized. Molecules B and B6 contained pyrrole and N-hexylpyrrole, respectively, as the central unit, which was connected to N,N-dimethylphenyl-4-azo on one side of the pyrrole molecule. Molecule A contained N-hexylpyrrole as the central unit, which was connected to anthracenyl-9-azo on one side of the pyrrole molecule. The other side of the pyrrole molecule was connected to cyanovinylene 4-nitrophenyl for all molecules. The long-wavelength absorption maximum of the molecules was located at 601-637 nm, and their optical band gap was 1.62-1.67 eV. The photovoltaic properties have been investigated using blends of B, B6, or A with PCBM, and it was found that the device based on A:PCBM had a higher power conversion efficiency (PCE) (2.06%) than the devices based on B:PCBM (1.33%) and B6:PCBM (1.36%). This has been attributed to the higher hole mobility, the lower band gap of A relative to that of B or B6, and the higher energy difference between the LUMO of A and PCBM. The effect of solvent annealing and thermal-solvent annealing on the photovoltaic response of the device based on the A:PCBM blend has been investigated, and it was found that the devices based on solvent-treated and subsequent thermally annealed blends have PCEs of 2.56 and 2.83%, respectively. The increase in the PCE has been attributed to the enhanced crystallinity of the blend and the improvement in the charge transport due to a reduction in the difference between the electron and hole mobility in the blend.

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New anthracene‐containing phenylene‐ or thienylene‐vinylene copolymers: Synthesis, characterization, photophysics, and photovoltaics

Cited by 6 publications

References 49 publications

Anthracene-Fused BODIPYs as Near-Infrared Dyes with High Photostability

Anthracene-Fused BODIPYs as Near-Infrared Dyes with High Photostability

Polymers with alternating anthracene and phenylene building blocks linked by ethynylene and/or vinylene units: Studying structure‐properties‐relationships

Bulk Heterojunction Photovoltaics Using Broadly Absorbing Small Molecules Based on 2-Styryl-5-phenylazo-pyrrole

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