Determination of the electronic structure of oligofurans and extrapolation to polyfuran

Distefano, Giuseppe; Jones, Derek; Guerra, Maurizio; Favaretto, Laura; Modelli, Alberto; Mengoli, G.

doi:10.1021/j100177a028

Cited by 76 publications

(60 citation statements)

References 2 publications

(4 reference statements)

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“…Apart from the gas phase IPs of Jones et al 25 there are also gas phase IPs for tetrathiophene through octithiophene 26 and for furan through tetrafuran. 27 However, only valence regions are available and the assignment of the peaks to individual states becomes more and more difficult because of band formation. In Figures 8 and 9 calculated and experimental peak positions according to deconvolution are compared for tetrafuran and octithiophene.…”

Section: Resultsmentioning

confidence: 99%

Modeling Photoelectron Spectra of Conjugated Oligomers with Time-Dependent Density Functional Theory

Salzner

2010

J. Phys. Chem. A

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With the aim of producing accurate band structures of conjugated systems by employing the states of cations, TDDFT calculations on conjugated oligomer radical cations of thiophene, furan, and pyrrole with one to eight rings were carried out. Benchmarking of density functional theory and ab initio methods on the thiophene monomer shows that the ∆SCF ionization potential (IP) is most accurate at the B3LYP/6-311G* level. Improvement of the basis set beyond 6-311G* leads to no further changes. The IP is closer to experiment at B3LYP/6-311G* than at CCSD(T)/CCPVQZ. For longer oligomers the ∆SCF IPs decrease too fast with increasing chain length with all density functionals. CCSD/6-311G* performs well if the geometries are optimized at the CCSD level. With MP2 geometries IPs decrease too fast. Peak positions in photoelectron spectra were determined by adding appropriate TDDFT excitation energies of radical cations to the ∆SCF IPs. The agreement with experiment and with Green function calculations shows that TDDFT excited states of radical cations at the B3LYP/6-311G* level are very accurate and that absorption energies can be employed to predict photoelectron spectra.

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Section: Resultsmentioning

confidence: 99%

Modeling Photoelectron Spectra of Conjugated Oligomers with Time-Dependent Density Functional Theory

Salzner

2010

J. Phys. Chem. A

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“…This can be explained by the decreasing electronegativity of the heteroatom. In order to produce the low-energy absorption band, the acceptor unit must be electron-deficient enough to produce a chargeseparated state [12]. As the electronegativity of the heteroatom decreases upon moving from S to Se, the acceptor unit's ability to separate charge and stabilize a charge-separated state decrease, leading to a decrease in the absorption coefficient of the low-energy band when moving from S to Se [40].…”

Section: Uv-vis Fluorescence Spectra and Solvatochromic Experimentsmentioning

confidence: 99%

“…of furans on the side reactions during the polymerization and low stability and poor properties of the resulting polymers [11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Furan and pyridinechalcogenodiazole-based π-conjugated systems via a donor-acceptor approach

Liu

Zhen

Ming

et al. 2016

J Solid State Electrochem

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Two novel furan and pyridinechalcogenodiazole based monomers, namely 4,7-di(furan-2-yl)-[1, 2, 5]thiadiazolo [3,4-c]pyridine (Fu-S-Fu) and 4,7-di(furan-2-yl)-[1, 2, 5]selenadiazolo [3,4-c]pyridine (Fu-Se-Fu), where a single atom in the pyridinechalcogenodiazole unit is varied from S to Se, were designed and synthesized via a donoracceptor approach, and then the corresponding polymers, P(Fu-S-Fu) and P(Fu-Se-Fu), were electrosynthesized. Also, structure characterization and optoelectronic properties, including FTIR, SEM, DFT theoretical calculations, intramolecular charge transfer nature, optical and electrochemical behaviors, and electrochromic performance, were systematically investigated and comparatively discussed. The obtained monomers exhibited lower oxidation potential (Fu-S-Fu: 1.12 V; Fu-Se-Fu: 1.09 V), leading to the facile electrodeposition of uniform hybrid polymer films with outstanding electroactivity at low oxidation potentials. Optical spectroscopy of corresponding polymers showed that Se substitution led to a redshift in the low-energy transition, while the high-energy band remains relatively constant in energy.

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“…4,6,9 In general there is not much structural information about this class the compounds. The structural information available is related to conformational studies and crystal structure as electronic interactions between oxygen of carbonyl group and the heteroatom 5,7,9 and interatomic interactions of type C-H…O, C-H…p, p…p 10,11 Following our interest in this kind of compounds, mainly directed to their use as potential ligands in further complex development we have synthesized and characterized a new compound in this populous family, viz: ir Spectrum Spectra of 1-(2-thienyl)-3-(3-methyl-2-thienyl)-propenone in KBr pellets were recorded on a FTIR-NICOLET MAGNA 550 spectrometer.…”

Section: 5mentioning

confidence: 99%

Structural Study of a New 1-(2-Thienyl)-3-(3-Methyl-2-Thienyl)-Propenone, in Situ Radiation-Induced Dimerization Products

Moreno

Contreras

Buljan

et al. 2010

J. Chil. Chem. Soc.

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The new conjugated system ("chalcone kind") reported herein, 1-(2-thienyl)-3-(3-methyl-2-thienyl)-propenone, C 12 H 10 OS 2 presents a monomeric molecular structure, and it most interesting aspects are to be found in it intermolecular interactions, of varied type (C-H···O, C-H···π, π···π) and strength. Some anomalies detected in the refinement process, however, provided evidence that an unexpected in-situ, radiation-induced dimerization reaction had taken place during data collection, with the starting and final products coexisting in a topotactic fashion. This effect is depended of structural packing; that is not all this kind of conjugated system presents this effect. The main factor is the distance between the double bonds of neighboring monomers (about 3 Å)

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Determination of the electronic structure of oligofurans and extrapolation to polyfuran

Cited by 76 publications

References 2 publications

Modeling Photoelectron Spectra of Conjugated Oligomers with Time-Dependent Density Functional Theory

Modeling Photoelectron Spectra of Conjugated Oligomers with Time-Dependent Density Functional Theory

Furan and pyridinechalcogenodiazole-based π-conjugated systems via a donor-acceptor approach

Structural Study of a New 1-(2-Thienyl)-3-(3-Methyl-2-Thienyl)-Propenone, in Situ Radiation-Induced Dimerization Products

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