Research Article
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Year 2024, Volume: 6 Issue: 1, 362 - 376, 16.03.2024

Abstract

References

  • Alvey P. M., Reczek J. J., Lynch V., and Iverson B. L. 2010. A Systematic Study of Thermochromic Aromatic Donor-Acceptor Materials. J. Org. Chem., 75, 7682–7690.
  • Chai S., Wen S., Huang J., and Han K. 2011. Density Functional Theory Study on Electron and Hole Transport Properties of Organic Pentacene Derivatives with Electron-Withdrawing Substituent. Journal of Computational Chemistry, 3218-3225.
  • Chakravarty M. and Vora A., 2021. Drug Delivery and Translational Research, 11, 748.
  • Chang Y. and Chao I. 2010. An Important Key to Design Molecules with Small Internal Reorganization Energy: Strong Nonbonding Character in Frontier Orbitals. J. Phys. Chem. Lett., 1, 116–121.
  • Cheng Y., Qi Y., Tang Y., Zheng C., Wan Y., Huang W., and Chen R. 2016. Controlling Intramolecular Conformation Through Nonbonding Interaction for Soft-Conjugated Materials: Molecular Design and Optoelectronic Properties. J. Phys. Chem. Lett., Just Accepted Manuscript.
  • Cias P., Slugovc C., and Gescheidt G. 2011. Hole Transport in Triphenylamine Based OLED Devices: From Theoretical Modeling to Properties Prediction. J. Phys. Chem. A, 115, 14519–14525.
  • Daswani U., Singh U., Sharma P., and Kumar A. 2018. From Molecules to Devices: A DFT/TD-DFT Study of Dipole Moment and Internal Reorganization Energies in Optoelectronically Active Aryl Azo Chromophores. J. Phys. Chem. C, Just Accepted Manuscript.
  • Gao H. 2010. Theoretical investigation into charge mobility in 4,40-bis(1-naphthylphenylamino) biphenyl. Theor. Chem. Acc. 127:759–763.
  • García-Frutos E. M., Gutierrez-Puebla E., Monge M. A., Ramírez R., Andrés P., Andrés A., Ramírez R., Gómez-Lor B. 2009. Crystal structure and charge transport properties of N-trimethyltriindole: Novel p-type organic semiconductor single crystals. Organic Electronics 10 643–652.
  • Gruhn N. E., Silva Filho D. A., Bill T. G., Malagoli M., Coropceanu V., Kahn A., and Bre´das J. 2002. The Vibrational Reorganization Energy in Pentacene: Molecular Influences on Charge Transport. J. Am. Chem. Soc., 124, 7918-7919.
  • Huang W., Xie W., Huang H., Zhang H., and Liu H. 2020. Designing Organic Semiconductors with Ultrasmall Reorganization Energies: Insights from Molecular Symmetry, Aromaticity and Energy Gap. J. Phys. Chem. Lett., Just Accepted Manuscript.
  • Huong V. T. T., Nguyen H. T., Tai T. B., and Nguyen M. T. 2013. π‑Conjugated Molecules Containing Naphtho[2,3‑b]thiophene and Their Derivatives: Theoretical Design for Organic Semiconductors. J. Phys. Chem. C, 117, 10175−10184.
  • Hutchison G. R., Ratner M. A., and Marks T. J. 2005. Intermolecular Charge Transfer between Heterocyclic Oligomers. Effects of Heteroatom and Molecular Packing on Hopping Transport in Organic Semiconductors. J. Am. Chem. Soc., 127, 16866-16881.
  • Irfan A., Al-Sehemi A. G., Aijaz Rasool Chaudhry A. R., Muhammad S. 2018. The structural, electro-optical, charge transport and nonlinear optical properties of oxazole (4Z)-4-Benzylidene-2-(4-methylphenyl)-1,3-oxazol- 5(4H)-one derivative. Journal of King Saud University – Science 30, 75–82.
  • Jia X., Wei H., Shi Y., Liu Y. 2019. Theoretical studies on charge transport and optical properties of diarylmaleic anhydride derivatives as organic light-emitting materials. Chemical Physics Letters 724 50–56.
  • Köse M. E., Mitchell W. J., Kopidakis N., Chang C. H., Shaheen S. E., Kim K., and Rumbles G. 2007. Theoretical Studies on Conjugated Phenyl-Cored Thiophene Dendrimers for Photovoltaic Applications. J. AM. CHEM. SOC., 129, 14257-14270.
  • Krishna G. R., Devarapalli R., Lal G., and Reddy C. M. 2016. Mechanically Flexible Organic Crystals Achieved by Introducing Weak Interactions in Structure: Supramolecular Shape Synthons. J. Am. Chem. Soc., 138, 13561−13567.
  • Li H X, Wang X F, Li Z F. 2012. Theoretical study of the effects of different substituents of tetrathiafulvalene derivatives on charge transport. Chin Sci Bull, 57: 4049-4056.
  • Liu Y., Sun X., Gahungu G., Qu X., Wang Y. and Wu Z. 2013. DFT/TDDFT investigation on the electronic structures and photophysical properties of phosphorescent Ir (III) complexes with conjugated/non-conjugated carbene ligands. J. Mater. Chem. C, 1, 3700.
  • McMahon D. P. and Troisi A. 2010. Evaluation of the External Reorganization Energy of Polyacenes. J. Phys. Chem. Lett., 1, 941–946.
  • Navamani K., Saranya G., Kolandaivel P. and Senthilkumar K. 2013. Effect of structural fluctuations on charge carrier mobility in thiophene, thiazole and thiazolothiazole based oligomers. Phys.Chem. Chem. Phys.15, 17947.
  • Nguyen T. P., Shim J. H., and Lee J. Y. 2015. Density Functional Theory Studies of Hole Mobility in Picene and Pentacene Crystals. J. Phys. Chem. C, Just Accepted Manuscript. Reed A. E., Carpenter J. E., and Weinhold F. 2014. NBO Version 3.1, E. D. Glendening.
  • Senevirathna W., Daddario C. M., and Sauvé G. 2014. Density Functional Theory Study Predicts Low Reorganization Energies for Azadipyrromethene-Based Metal Complexes. J. Phys. Chem. Lett., 5, 935−941.
  • Siddiqui S. A., Al-Hajry A., and Al-Assiri M. S. 2016. Ab Initio Investigation of 2,20-Bis(4-trifluoromethylphenyl)- 5,50-Bithiazole for the Design of Efficient Organic Field-Effect Transistors. International Journal of Quantum Chemistry, 116, 339–345.
  • Swicka S. M., Zhua W., Mattaa M., Aldricha T. J., Harbuzaruc A., Navarretec J. T. L., Ortizc R. P., Kohlstedta K. L., Schatza G. C., Facchettia A., Melkonyana F. S., and Marks T. J. 2018. Closely packed, low reorganization energy π-extended postfullerene acceptors for efficient polymer solar cells. PNAS Latest Articles.
  • Tan Y., Casetti N. C., Boudouris B. W., and Savoie B. M. 2021. Molecular Design Features for Charge Transport in Nonconjugated Radical Polymers. J. Am. Chem. Soc., 143, 11994−12002.
  • Tripathi A., Prabhakar C. 2019. Optoelectronic and charge‐transport properties of truxene, isotruxene, and its heteroatomic (N, O, Si, and S) analogs: A DFT study. J Phys Org Chem.; 32: e3944.
  • Wang C., Dong H., Jiang L. and Hu W. 2018. Organic semiconductor crystals. Chem. Soc. Rev., ,47, 422.
  • Wang L., Duan G., Ji Y., and Zhang H. 2012. Electronic and Charge Transport Properties of peri- Xanthenoxanthene: The Effects of Heteroatoms and Phenyl Substitutions. J. Phys. Chem. C, 116, 22679−22686.
  • Wang L., Li T., Shen Y., and Song Y. 2016. A theoretical study of electronic structure and charge transport property for thieno[2,3-b] benzothiophene based derivatives. Phys. Chem.
  • Chem. Phys. Qi Y., Chen C., Zheng C., Tang Y., Wan Y., Jiang H., Chen T., Tao Y. and Chen R. 2020. Heteroatom-bridged Heterofluorenes: A Theoretical Study on Molecular Structures and Optoelectronic Properties Phys. Chem. Chem. Phys., 00, 1-3.
  • Yan L., Zhao Y., Yu H., Hu Z., He Y., Li A., Goto O., Yan C., Chen T., Chen R., Loo L., Perepichka D., Meng H. and Huang, W.J. 2013. Influence of Heteroatoms on the Charge Mobility of Anthracene Derivatives. J. Name., 00, 1-3 | 1.
  • Yang L., Mao J., Yin C., Mohamad A. A., Wu X., Dong C., Liu Y., Wei Y., Xie L., Ran X. and Huang W. 2019. Novel Structure of Grid Spirofluorene: A New Organic Semiconductor with Low Reorganization Energy. J. Name., 2013, 00, 1-3 | 1.
  • Yang X., Wang L., Wang C., Long W., and Shuai Z. 2008. Influences of Crystal Structures and Molecular Sizes on the Charge Mobility of Organic Semiconductors: Oligothiophenes. Chem. Mater., Vol. 20, No. 9.
  • Zhang D., Xu F., Lu Q., Zhang R., Xia J. 2023. Poly(3-amino-carbazole) derivatives containing 1,10-phenanthroline and 8-hydroxyquinoline ligands: Synthesis, properties and application as ion sensors. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 295.
  • Zhang M. and Zhao G. 2012. Heteroatomic Effects on Charge-Transfer Mobility of Dianthra [2,3-b:2′,3′-f] thieno[3,2-b] thiophene (DATT) and Its Derivatives. J. Phys. Chem. C, 116, 19197−19202.
  • Zhu R., Duan Y., Geng Y., Wei C., Chen X., Liao Y. 2016. Theoretical evaluation on the reorganization energy of five-ring-fused benzothiophene derivatives. Computational and Theoretical Chemistry 1078 16–22.
  • Zhang Y., Cai X., Bian Y., Li X., and Jiang J. 2008. Heteroatom Substitution of Oligothienoacenes: From Good p-Type Semiconductors to Good Ambipolar Semiconductors for Organic Field-Effect Transistors. J. Phys. Chem. C, 112, 5148-5159.

Estimation of the Charge Mobility of Phenanthroline derivatives with the view of Density Functional Theory: Reorganization Energy and Charge Transfer Integral are in play

Year 2024, Volume: 6 Issue: 1, 362 - 376, 16.03.2024

Abstract

Molecular arrangement and noncovalent interactions in organic materials greatly influence the charge mobility in organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and organic field-effect transistors (OFETs). In the light of the this argument, we examined the electronic properties of the phenanthroline derivatives by considering the charge mobility with the combination of density functional theory and Marcus Charge Transfer Theory. The drift electron mobility of the molecule 1 and 2 were determined to 21.13 cm2 V-1 s-1 and 18.00 cm2 V-1 s-1, respectively through J type π⋯π stacking interactions created by small perpendicular distances between the adjacent rings. The effective charge pathways of the molecules were generated with strong π⋯π stacking interactions consolidated by noncovalent interactions in their solid phases. The electron reorganization energy for both molecules were determined smaller than that of holes which means they have n-type semiconductor properties. The charge transfer integrals were calculated with the optimization of molecules’ dimer configurations that the theoretical results demonstrate the charge transfer integral depends on the distance between the stacking rings. High charge transfer integral and small reorganization energy give the high charge mobility fort he semiconductor molecules. Beside the mobility, energy band gap, ionization potential, electron and hole injection barriers of the molecules were interpreted to further understand their electronic properties. Due to the small LUMO values which provide n-type molecule and small electron injection barrier. From the our work both molecules can be effective n type organic semiconductor devices with the high mobility and can be modified for more efficient charge transport in phenanthroline derivatives.

References

  • Alvey P. M., Reczek J. J., Lynch V., and Iverson B. L. 2010. A Systematic Study of Thermochromic Aromatic Donor-Acceptor Materials. J. Org. Chem., 75, 7682–7690.
  • Chai S., Wen S., Huang J., and Han K. 2011. Density Functional Theory Study on Electron and Hole Transport Properties of Organic Pentacene Derivatives with Electron-Withdrawing Substituent. Journal of Computational Chemistry, 3218-3225.
  • Chakravarty M. and Vora A., 2021. Drug Delivery and Translational Research, 11, 748.
  • Chang Y. and Chao I. 2010. An Important Key to Design Molecules with Small Internal Reorganization Energy: Strong Nonbonding Character in Frontier Orbitals. J. Phys. Chem. Lett., 1, 116–121.
  • Cheng Y., Qi Y., Tang Y., Zheng C., Wan Y., Huang W., and Chen R. 2016. Controlling Intramolecular Conformation Through Nonbonding Interaction for Soft-Conjugated Materials: Molecular Design and Optoelectronic Properties. J. Phys. Chem. Lett., Just Accepted Manuscript.
  • Cias P., Slugovc C., and Gescheidt G. 2011. Hole Transport in Triphenylamine Based OLED Devices: From Theoretical Modeling to Properties Prediction. J. Phys. Chem. A, 115, 14519–14525.
  • Daswani U., Singh U., Sharma P., and Kumar A. 2018. From Molecules to Devices: A DFT/TD-DFT Study of Dipole Moment and Internal Reorganization Energies in Optoelectronically Active Aryl Azo Chromophores. J. Phys. Chem. C, Just Accepted Manuscript.
  • Gao H. 2010. Theoretical investigation into charge mobility in 4,40-bis(1-naphthylphenylamino) biphenyl. Theor. Chem. Acc. 127:759–763.
  • García-Frutos E. M., Gutierrez-Puebla E., Monge M. A., Ramírez R., Andrés P., Andrés A., Ramírez R., Gómez-Lor B. 2009. Crystal structure and charge transport properties of N-trimethyltriindole: Novel p-type organic semiconductor single crystals. Organic Electronics 10 643–652.
  • Gruhn N. E., Silva Filho D. A., Bill T. G., Malagoli M., Coropceanu V., Kahn A., and Bre´das J. 2002. The Vibrational Reorganization Energy in Pentacene: Molecular Influences on Charge Transport. J. Am. Chem. Soc., 124, 7918-7919.
  • Huang W., Xie W., Huang H., Zhang H., and Liu H. 2020. Designing Organic Semiconductors with Ultrasmall Reorganization Energies: Insights from Molecular Symmetry, Aromaticity and Energy Gap. J. Phys. Chem. Lett., Just Accepted Manuscript.
  • Huong V. T. T., Nguyen H. T., Tai T. B., and Nguyen M. T. 2013. π‑Conjugated Molecules Containing Naphtho[2,3‑b]thiophene and Their Derivatives: Theoretical Design for Organic Semiconductors. J. Phys. Chem. C, 117, 10175−10184.
  • Hutchison G. R., Ratner M. A., and Marks T. J. 2005. Intermolecular Charge Transfer between Heterocyclic Oligomers. Effects of Heteroatom and Molecular Packing on Hopping Transport in Organic Semiconductors. J. Am. Chem. Soc., 127, 16866-16881.
  • Irfan A., Al-Sehemi A. G., Aijaz Rasool Chaudhry A. R., Muhammad S. 2018. The structural, electro-optical, charge transport and nonlinear optical properties of oxazole (4Z)-4-Benzylidene-2-(4-methylphenyl)-1,3-oxazol- 5(4H)-one derivative. Journal of King Saud University – Science 30, 75–82.
  • Jia X., Wei H., Shi Y., Liu Y. 2019. Theoretical studies on charge transport and optical properties of diarylmaleic anhydride derivatives as organic light-emitting materials. Chemical Physics Letters 724 50–56.
  • Köse M. E., Mitchell W. J., Kopidakis N., Chang C. H., Shaheen S. E., Kim K., and Rumbles G. 2007. Theoretical Studies on Conjugated Phenyl-Cored Thiophene Dendrimers for Photovoltaic Applications. J. AM. CHEM. SOC., 129, 14257-14270.
  • Krishna G. R., Devarapalli R., Lal G., and Reddy C. M. 2016. Mechanically Flexible Organic Crystals Achieved by Introducing Weak Interactions in Structure: Supramolecular Shape Synthons. J. Am. Chem. Soc., 138, 13561−13567.
  • Li H X, Wang X F, Li Z F. 2012. Theoretical study of the effects of different substituents of tetrathiafulvalene derivatives on charge transport. Chin Sci Bull, 57: 4049-4056.
  • Liu Y., Sun X., Gahungu G., Qu X., Wang Y. and Wu Z. 2013. DFT/TDDFT investigation on the electronic structures and photophysical properties of phosphorescent Ir (III) complexes with conjugated/non-conjugated carbene ligands. J. Mater. Chem. C, 1, 3700.
  • McMahon D. P. and Troisi A. 2010. Evaluation of the External Reorganization Energy of Polyacenes. J. Phys. Chem. Lett., 1, 941–946.
  • Navamani K., Saranya G., Kolandaivel P. and Senthilkumar K. 2013. Effect of structural fluctuations on charge carrier mobility in thiophene, thiazole and thiazolothiazole based oligomers. Phys.Chem. Chem. Phys.15, 17947.
  • Nguyen T. P., Shim J. H., and Lee J. Y. 2015. Density Functional Theory Studies of Hole Mobility in Picene and Pentacene Crystals. J. Phys. Chem. C, Just Accepted Manuscript. Reed A. E., Carpenter J. E., and Weinhold F. 2014. NBO Version 3.1, E. D. Glendening.
  • Senevirathna W., Daddario C. M., and Sauvé G. 2014. Density Functional Theory Study Predicts Low Reorganization Energies for Azadipyrromethene-Based Metal Complexes. J. Phys. Chem. Lett., 5, 935−941.
  • Siddiqui S. A., Al-Hajry A., and Al-Assiri M. S. 2016. Ab Initio Investigation of 2,20-Bis(4-trifluoromethylphenyl)- 5,50-Bithiazole for the Design of Efficient Organic Field-Effect Transistors. International Journal of Quantum Chemistry, 116, 339–345.
  • Swicka S. M., Zhua W., Mattaa M., Aldricha T. J., Harbuzaruc A., Navarretec J. T. L., Ortizc R. P., Kohlstedta K. L., Schatza G. C., Facchettia A., Melkonyana F. S., and Marks T. J. 2018. Closely packed, low reorganization energy π-extended postfullerene acceptors for efficient polymer solar cells. PNAS Latest Articles.
  • Tan Y., Casetti N. C., Boudouris B. W., and Savoie B. M. 2021. Molecular Design Features for Charge Transport in Nonconjugated Radical Polymers. J. Am. Chem. Soc., 143, 11994−12002.
  • Tripathi A., Prabhakar C. 2019. Optoelectronic and charge‐transport properties of truxene, isotruxene, and its heteroatomic (N, O, Si, and S) analogs: A DFT study. J Phys Org Chem.; 32: e3944.
  • Wang C., Dong H., Jiang L. and Hu W. 2018. Organic semiconductor crystals. Chem. Soc. Rev., ,47, 422.
  • Wang L., Duan G., Ji Y., and Zhang H. 2012. Electronic and Charge Transport Properties of peri- Xanthenoxanthene: The Effects of Heteroatoms and Phenyl Substitutions. J. Phys. Chem. C, 116, 22679−22686.
  • Wang L., Li T., Shen Y., and Song Y. 2016. A theoretical study of electronic structure and charge transport property for thieno[2,3-b] benzothiophene based derivatives. Phys. Chem.
  • Chem. Phys. Qi Y., Chen C., Zheng C., Tang Y., Wan Y., Jiang H., Chen T., Tao Y. and Chen R. 2020. Heteroatom-bridged Heterofluorenes: A Theoretical Study on Molecular Structures and Optoelectronic Properties Phys. Chem. Chem. Phys., 00, 1-3.
  • Yan L., Zhao Y., Yu H., Hu Z., He Y., Li A., Goto O., Yan C., Chen T., Chen R., Loo L., Perepichka D., Meng H. and Huang, W.J. 2013. Influence of Heteroatoms on the Charge Mobility of Anthracene Derivatives. J. Name., 00, 1-3 | 1.
  • Yang L., Mao J., Yin C., Mohamad A. A., Wu X., Dong C., Liu Y., Wei Y., Xie L., Ran X. and Huang W. 2019. Novel Structure of Grid Spirofluorene: A New Organic Semiconductor with Low Reorganization Energy. J. Name., 2013, 00, 1-3 | 1.
  • Yang X., Wang L., Wang C., Long W., and Shuai Z. 2008. Influences of Crystal Structures and Molecular Sizes on the Charge Mobility of Organic Semiconductors: Oligothiophenes. Chem. Mater., Vol. 20, No. 9.
  • Zhang D., Xu F., Lu Q., Zhang R., Xia J. 2023. Poly(3-amino-carbazole) derivatives containing 1,10-phenanthroline and 8-hydroxyquinoline ligands: Synthesis, properties and application as ion sensors. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 295.
  • Zhang M. and Zhao G. 2012. Heteroatomic Effects on Charge-Transfer Mobility of Dianthra [2,3-b:2′,3′-f] thieno[3,2-b] thiophene (DATT) and Its Derivatives. J. Phys. Chem. C, 116, 19197−19202.
  • Zhu R., Duan Y., Geng Y., Wei C., Chen X., Liao Y. 2016. Theoretical evaluation on the reorganization energy of five-ring-fused benzothiophene derivatives. Computational and Theoretical Chemistry 1078 16–22.
  • Zhang Y., Cai X., Bian Y., Li X., and Jiang J. 2008. Heteroatom Substitution of Oligothienoacenes: From Good p-Type Semiconductors to Good Ambipolar Semiconductors for Organic Field-Effect Transistors. J. Phys. Chem. C, 112, 5148-5159.
There are 38 citations in total.

Details

Primary Language English
Subjects Reaction Kinetics and Dynamics
Journal Section Research Articles
Authors

Zeynep Türkmen Bulca

Gül Yakalı

Publication Date March 16, 2024
Published in Issue Year 2024 Volume: 6 Issue: 1

Cite

APA Türkmen Bulca, Z., & Yakalı, G. (2024). Estimation of the Charge Mobility of Phenanthroline derivatives with the view of Density Functional Theory: Reorganization Energy and Charge Transfer Integral are in play. International Journal of Science Letters, 6(1), 362-376.
AMA Türkmen Bulca Z, Yakalı G. Estimation of the Charge Mobility of Phenanthroline derivatives with the view of Density Functional Theory: Reorganization Energy and Charge Transfer Integral are in play. IJSL. March 2024;6(1):362-376.
Chicago Türkmen Bulca, Zeynep, and Gül Yakalı. “Estimation of the Charge Mobility of Phenanthroline Derivatives With the View of Density Functional Theory: Reorganization Energy and Charge Transfer Integral Are in Play”. International Journal of Science Letters 6, no. 1 (March 2024): 362-76.
EndNote Türkmen Bulca Z, Yakalı G (March 1, 2024) Estimation of the Charge Mobility of Phenanthroline derivatives with the view of Density Functional Theory: Reorganization Energy and Charge Transfer Integral are in play. International Journal of Science Letters 6 1 362–376.
IEEE Z. Türkmen Bulca and G. Yakalı, “Estimation of the Charge Mobility of Phenanthroline derivatives with the view of Density Functional Theory: Reorganization Energy and Charge Transfer Integral are in play”, IJSL, vol. 6, no. 1, pp. 362–376, 2024.
ISNAD Türkmen Bulca, Zeynep - Yakalı, Gül. “Estimation of the Charge Mobility of Phenanthroline Derivatives With the View of Density Functional Theory: Reorganization Energy and Charge Transfer Integral Are in Play”. International Journal of Science Letters 6/1 (March 2024), 362-376.
JAMA Türkmen Bulca Z, Yakalı G. Estimation of the Charge Mobility of Phenanthroline derivatives with the view of Density Functional Theory: Reorganization Energy and Charge Transfer Integral are in play. IJSL. 2024;6:362–376.
MLA Türkmen Bulca, Zeynep and Gül Yakalı. “Estimation of the Charge Mobility of Phenanthroline Derivatives With the View of Density Functional Theory: Reorganization Energy and Charge Transfer Integral Are in Play”. International Journal of Science Letters, vol. 6, no. 1, 2024, pp. 362-76.
Vancouver Türkmen Bulca Z, Yakalı G. Estimation of the Charge Mobility of Phenanthroline derivatives with the view of Density Functional Theory: Reorganization Energy and Charge Transfer Integral are in play. IJSL. 2024;6(1):362-76.