DFT study of molecular structure and electronic properties of fluoromethylpyrrole oligomers including di-, tri- and tetramer

Nikoofard, Hossein; Sabzyan, Hassan

doi:10.1016/j.jfluchem.2007.03.006

Cited by 11 publications

(10 citation statements)

References 27 publications

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“…The first step in the electropolymerization of conducting polymers is formation of intermediate radical cations from monomers which can be considered as an ionization reaction [ 37 ]. …”

Section: Resultsmentioning

confidence: 99%

Theoretical study on the electronic, structural, properties and reactivity of a series of mono-, di-, tri- and tetrachlorothiophenes as well as corresponding radical cation forms as monomers for conducting polymers

Beigi

Jameh‐Bozorghi

2011

Chemistry Central Journal

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In this paper, electrical and structural properties of mono-, di-, tri- and tetrachlorothiophenes and their radical cations have been studied using the density functional theory and B3LYP method with 6-311++G** basis set. The effects of the number and position of the substituent of chlorine atoms on the properties of the thiophene ring for all chlorothiophenes and their radical cations have been studied. Vibrational frequencies, nuclear chemical shielding constants, spin-density distribution, size and direction of dipole moment vector, ionization potential, electric polarizabilities and NICS values of these compounds have been calculated as well. The analysis of these data showed that double bonds in 3-chlorothiophene are more delocalized and it is the best possible candidate monomer among all chlorothiophenes for the synthesis of corresponding conducting polymers with modified characteristics.

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“…The first step in the electropolymerization of conducting polymers is formation of intermediate radical cations from monomers which can be considered as an ionization reaction [ 37 ]. …”

Section: Resultsmentioning

confidence: 99%

Theoretical study on the electronic, structural, properties and reactivity of a series of mono-, di-, tri- and tetrachlorothiophenes as well as corresponding radical cation forms as monomers for conducting polymers

Beigi

Jameh‐Bozorghi

2011

Chemistry Central Journal

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“…In addition to their orientations, size of the electric dipole moment vector of the monomers and their interactions with the solvent and support electrolyte are the key factors in their selection for electro-polymerization. Furthermore, the structure of the electrical double layer at the surface of electrodes which determines the kinetics of the diffusion-controlled electrode reactions depends on the dipole moment of the solute molecules [20,23]. Thus, the calculated values of the electric dipole moment vectors for FMF monomers and their corresponding oligomers have been listed in Table 3.…”

Section: Dipole Moments Of the Oligomersmentioning

confidence: 99%

“…The comparative size of the dipole moment vectors for all of monomers and their oligomers with the same size follows: Fu-CH 2 F < Fu-CHF 2 < Fu-CF 3 According to this trend, the oligomers consisting of Fu-CF 3 oligomers are expected to be more soluble in polar solvents because of the larger electric dipole moments. Also, it is observed (Table 4) that the electron donor characters of the -CH 3 substituent decreases the dipole moment vector of the methylfuran oligomers, if the furan oligomers are taken as references as it was observed for fluoromethylpyrrole [20] and CMFs [11]. …”

Section: Dipole Moments Of the Oligomersmentioning

confidence: 99%

“…Since, the planarity of polymers chain is a necessary factor for electrical conducting of polymers [8,18,19]. The FMFs would be more conductive as compared to corresponding CMFs [11] but less conductive than fluoromethylpyrroles due to higher D Ri-Rj values [20]. However, the results show that the Fu-CF 3 oligomer would be more preferable structure for electro-polymerization synthesis of conducting polymer of furan derivatives as compared to furan and chloromethylfuran.…”

Section: Introductionmentioning

confidence: 99%

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Comformational Analysis and Electronic Properties of Fluoromethylfuran Oligomers: Semiempirical and DFT Study

Semire¹,

Adejoro

Odunola

2017

Eclet. Quim. J.

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Structural and electronic properties of oligomers of fluoromethylfurans (FMFs), OC4H4-CHnF3-n with n = 1, 2, 3 and 4 have been studied using ZINDO/AM1 and B3LYP/6-31G(d) basis set. Preliminary study using AM1 and ab initio (HF) 6-31G(d) with medium basis set was carried out on di-, tri- and tetramer FMFs in order to investigate the stability of configuration of the polymer chains and conformation analysis of the dimers. There is noticeable effect of substituents on the geometries of FMFs as compared to polyfuran, polymethylfuran and chloromethylfuran (CMF) analogues [11]as well as improved characteristics as conducting polymers compared polymethylfurans and CMFs. The most stable conformation is the anti-planar conformation except in fluoromethylfuran in which antigauche conformation is most stable. The energy band gaps, electronic spectroscopy and electronic dipole moment vectors of the compounds are presented. Generally FMFs present lower energy band gaps, longer wavelength and higher electric dipole moments and are therefore more suitable as monomer for conducting polymer especially trifluoromethylfuran.

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“…[20][21][22][23][24][25][26][27] Theoretical investigations carried out on a series of substituted thiophenes are, thereby, desirable for designing novel functional materials, and this is the main purpose of the current work. In the previous works, [28][29][30][31] we have studied a series of substituted pyrroles and thiophenes as potential monomers for the synthesis of conductive polymers and the corresponding oligomers with modified physical and electrical characteristics. In this work, we carried out a thermodynamic study of β-alkylthiophenes (ATs), whose structural formulas are depicted in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Computational Thermo-chemical Study of Enthalpies of formation of β-Alkylthiophenes Using Ab Initio and DFT Calculations

Nikoofard

2015

ACSi

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The values for the standard molar enthalpies of formation of a series of the β-ring position alkyl-substituted thiophenes are calculated at 298.15 K using the Hartree-Fock (HF) and density functional theory (DFT) calculations. The results obtained are discussed in terms of the substituent effect on the structural, electronic, and energetics of the titled molecules. In the atomization energy route, the values for the standard enthalpies of formation of these compounds in the gas phase,ΔH°f ,298 , obtained using the B3LYP/6-31G(d,p) level of theory, can be successfully correlated to the substituent length via an excellent linear dependence. However, the ΔH°f ,298 (g) values (g) obtained using the HF/6-31G(d,p) level of theory are not able to predict the experimental behavior of the alkyl thiophenes (ATs). In the formation reaction route, both the DFT and HF calculations reveal the same trend for the predicted values for the standard enthalpies of formation of these compounds in the condensed phase. It could be anticipated that the proposed method can be extended to estimate the relative thermodynamic stabilities of the oligomers and polymers consisting of these building blocks.

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DFT study of molecular structure and electronic properties of fluoromethylpyrrole oligomers including di-, tri- and tetramer

Cited by 11 publications

References 27 publications

Theoretical study on the electronic, structural, properties and reactivity of a series of mono-, di-, tri- and tetrachlorothiophenes as well as corresponding radical cation forms as monomers for conducting polymers

Theoretical study on the electronic, structural, properties and reactivity of a series of mono-, di-, tri- and tetrachlorothiophenes as well as corresponding radical cation forms as monomers for conducting polymers

Comformational Analysis and Electronic Properties of Fluoromethylfuran Oligomers: Semiempirical and DFT Study

Computational Thermo-chemical Study of Enthalpies of formation of β-Alkylthiophenes Using Ab Initio and DFT Calculations

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