Effects of Electron Withdrawing Groups on Transfer Integrals, Mobility, Electronic and Photo-Physical Properties of Naphtho[2,1-b:6,5-b′]Difuran Derivatives: A Theoretical Study

Chaudhry, Aijaz Rasool; Ahmed, Rashid; Irfan, Ahmad; Shaari, A.

doi:10.1166/sam.2014.1916

Cited by 25 publications

(19 citation statements)

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“…The computed value [37] of E HOMO was found in a healthy agreement with the experimental reported value of E HOMO for the parent molecule DPNDF [25]. Similarly our calculated value for the hole reorganization energy λ(h) [37] was in good agreement with already reported λ(h) [25] for DPNDF calculated at B3LYP/6-31G* level of theory.…”

Section: Computational Detailssupporting

confidence: 90%

“…For excited states (S 1 ), TD-DFT approach is used to optimize the relevant geometry of the each derivative at the TD-B3LYP/6-31G** [47][48][49][50][51][52] level of theory. In our previous study [37] the parent molecule DPNDF was optimized using the hybrid exchange and correlation functional B3LYP with the 6-31G** basis set. We found good agreement between the geometrical parameters (bond lengths, bond angles, dihedral angles) of the optimized geometries and experimental crystal structure [25].…”

Section: Computational Detailsmentioning

confidence: 99%

“…The eigenvalue and Kohn-Sham orbital (ε and C) were obtained from the Fock matrix of zeroth-order through "diagonalizing the Fock matrix without any self-consistent field iteration" [63]. For intermolecular transfer integrals investigations, the Fock matrix of the dimers with molecular orbit of unperturbed monomer have been directly evaluated at the PW91/6-31G** level of theory using Gaussian09 package and our own homemade code which has already been applied successfully [64][65][66][67][68][69][70][71]. This functional has been reported for giving the best description of intermolecular transfer integral term by Huang and Kertesz [72].…”

Section: Computational Detailsmentioning

confidence: 99%

“…Additionally, it is also expected that by doping or push-pull strategy crystal structure of the compound alter the space group, cell parameters and symmetry etc. However, previously, we have used DREIDING FF on S and Se containing systems to simulate the crystal structures and energy minimization [64][65][66][67] and found it a reasonable choice for energy minimization if the cell parameters did not alter. Finally, the aim of simulation is to minimize the crystal energy and gain packing which would be helpful to select the dimers and to evaluate the transfer integrals and mobilities.…”

Section: Crystal Packing Simulationsmentioning

confidence: 99%

“…In our earlier study, furan ring with a very low electron reorganization energy λ (e) [36] was analyzed as a good electron transport material. Two furan rings containing DPNDF [25] has been used as parent molecule and the effects of electron withdrawing groups (EWGs) [37,38], heteroatoms substitution [39], push-pull strategy [40] and increasing conjugation [41] were investigated in our previous studies.…”

Section: Introductionmentioning

confidence: 99%

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Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

et al. 2015

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The present study spotlights the designing of new derivatives of 2,7-bis (4-octylphenyl) naphtho [2,1-b:6,5-b'] difuran (C8-DPNDF) by substituting the alkyl groups (methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl groups) at para position. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods are employed to optimize the molecular structures in ground and first excited states, respectively. Several electro-optical properties including hole/electron reorganization energies (λh/λe), electron affinities (EAs), ionization potentials (IPs), molecular electrostatic potentials (MEP), and frontier molecular orbitals (FMOs) have been evaluated. Furthermore their transfer integrals and intrinsic mobilities values have also been calculated. From this study, it is found that hole mobility of octyl containing derivative is raised to 4.69 cm(2) V(-1) s(-1). Moreover with attaching octyl group, hole transfer integral values have also been enhanced in newly designed derivatives. The balanced hole and electron reorganization energies, and improved transfer integrals lead to enhanced mobility in derivatives with octyl group, highlighting them as an efficient hole transfer material. Unlike the other electro-optical properties, the intrinsic hole mobility has increased because of transfer integral values of octyl containing derivative C8-DPNDF due to the dense and close crystal packing of C8-DPNDF. However, photostability of furan-based materials has not changed by increasing length of extended alkyl chain. Thus our present investigation highlights the importance of alkyl auxiliary groups that are often neglected/replaced with simple methyl group to save computation costs. Graphical Abstract The hole and electron reorganization energies of naphtho[2,1-b:6,5-b']difuran derivatives.

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Section: Computational Detailssupporting

confidence: 90%

Section: Computational Detailsmentioning

confidence: 99%

Section: Computational Detailsmentioning

confidence: 99%

Section: Crystal Packing Simulationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

et al. 2015

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How does the increment of hetero-cyclic conjugated moieties affect electro-optical and charge transport properties of novel naphtha-difuran derivatives? A computational approach

et al. 2014

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We have investigated computationally the effects of π-conjugation extension on naphtha[2,1-b:6,5-b'] difuran (DPNDF); where we increase the number of fused NDF (central core) and furan rings in the parent molecule. The molecular structures of all analogues have been optimized at the ground (S0) and first excited (S1) states using density functional theory (DFT) and time-dependent density functional theory (TD-DFT), respectively. Then highest occupied molecular orbitals (HOMOs), the lowest unoccupied molecular orbitals (LUMOs), photophysical properties, adiabatic/vertical electron affinities (EAa)/(EAv), adiabatic/vertical ionization potentials (IPa)/(IPv), and hole/electron reorganization energies λh/λe have been investigated. The effect of NDF and furan rings on structural and electro-optical properties has also been studied. Our calculated reorganization energies of 1a, 1b, and 2c reveal them, materials with balanced hole/electron charge transport, whereas 2a and 2b are good hole-transport materials. By increasing the number of furan rings; the photostability was augmented in 2a, 2b, and 2c.

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Optoelectronic properties of naphtho[2, 1-b:6, 5-b′]difuran derivatives for photovoltaic application: a computational study

et al. 2016

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Some important optoelectronic properties of naphtho[2,1-b:6,5-b']difuran (DPNDF) and its two derivatives have been limelighted by applying the density functional theory (DFT). Due to their low cost, high stability and earth abundance, the DPNDF and its derivatives are considered as potential organic semiconductor materials for their optoelectronics applications. Highly proficient derivatives are obtained systematically by attaching -CN (cyanide) to DPNDF at various sites. Our calculations indicate that DPNDF has a wide and direct band gap with an energy gap of 3.157 eV. Whereas the band gaps of its derivatives are found to be decreased by 88 meV for derivative "a" and 300 meV for derivative "b" as a consequence of p orbitals present in C and N atoms in derivative structures. The narrowing of the energy gap and density of states for the derivatives of DPNDF in the present investigation suggest that energy gap can be engineered for desirable optoelectronic applications via derivatives designing. Furthermore, their obtained results for optical parameters such as the dielectric and conductivity functions, reflectivity, refractive index, and the extinction coefficients endorses their aptness for optoelectronic applications. Graphical Abstract Real part of dielectric function for derivative "b".

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Effects of Electron Withdrawing Groups on Transfer Integrals, Mobility, Electronic and Photo-Physical Properties of Naphtho[2,1-b:6,5-b′]Difuran Derivatives: A Theoretical Study

Cited by 25 publications

References 0 publications

Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

How does the increment of hetero-cyclic conjugated moieties affect electro-optical and charge transport properties of novel naphtha-difuran derivatives? A computational approach

Optoelectronic properties of naphtho[2, 1-b:6, 5-b′]difuran derivatives for photovoltaic application: a computational study

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