Chemical modification and doping of poly(p-phenylenes): A theoretical study

Zhang Q, Liu L, Pan C, Li D (2018) Review of recent achievements in self-healing conductive materials and their applications. J Mater Sci 53:27–46

Palma F, Cattaruzza E, Riello P (2019) Growth of nanostructured silicon by microwave/nano-susceptors technique with low substrate temperature. Mat Sci Semicon Proc 100:22–28

Rasmussen SC (2020) Conjugated and conducting organic polymers: the first 150 years. ChemPlusChem 85:1412–1429

Yanilmaz M, Sarac AS (2014) A review: effect of conductive polymers on the conductivities of electrospun mats. Text Res J 84:1325–1342

Kausar A (2016) Review on structure, properties and appliance of essential conjugated polymers. Am J Polym Sci Eng 4:91–102

Qiu ZJ, Hammer BAG, Müllen K (2020) Conjugated polymers – Problems and promises. Prog Polym Sci 100:101179

Vangari M, Pryor T, Jiang L (2013) Supercapacitors: review of materials and fabrication methods. J Energy Eng 139:72–79

Knopfmacher O et al (2014) Highly stable organic polymer field-effect transistor sensor for selective detection in the marine environment. Nat Commun 5:1–9

Zhong H, Er D, Dong L, Wen L (2017) Theoretical study on the poly(m-phenylene) derivatives with lower HOMO–LUMO gaps. Synth Met 229:16–21

Le TH, Kim Y, Yoon H (2017) Electrical and electrochemical properties of conducting polymers. Polymers 9:150

Cao X, Zhao K, Chen L, Liu J, Han Y (2019) Conjugated polymers single crystals and nanowires. Polym Cryst 2:e10064

Xia H et al (2019) Advances in conjugated polymers lasers. Polymers 11:443

Magu TO, Agobi AU, Hitler L, Dass PM (2019) A review on conducting polymers-based composites for energy storage application. J Chem Rev 1:19–34

Janjua MRSA (2021) How does bridging core modification alter the photovoltaic characteristics of triphenylamine-based hole transport material? theoretical understanding and predition. Chem Eur J 27:4197–4210

Ramanavicius S, Ramanavicius A (2021) Conducting polymers in the design of biosensors and biofuel cells. Polymers 13:49

Mehboob MY et al (2022) Theoretical modelling of novel indandione-based donor molecules for organic solar cell applications. J Phys Chem Solids 162:110508

Janjua MRSA (2022) Photovoltaic properties and enhancement in near-infrared light absorption capabilities of acceptor materials for organic solar cell applications: A quantum chemical perspective via DFT. J Phys Chem Solids 171:110996

Liu Y, Gao S, Zhang X, Xi JH, Zhang C (2023) Probing the nature of charge carriers in one-dimensional conjugated polymers: a review of the theoretical models, experimental trends, and thermoelectric applications. J Mater Chem C 11:12–47

Pooja KA, Prashe P, Mudila H (2023) Factors affecting the electrical conductivity of conducting polymers. Carbon Lett 33:307–324

van Mullekon HAM, Vekemans JAJM, Havinga EE, Meijer EW (2001) Developments in the chemistry and band gap engineering of donor-acceptor substituted conjugated polymers. Mater Sci Eng 32:1–40

Roncali J (2007) Molecular engineering of the band gap of π-conjugated systems: facing technological applications. Macromol Rapid Commun 28:1761–1775

Bures F (2014) Fundamental aspects of property tuning in push-pull molecules. RSC Adv 4:58526–58851

Wu JS, Cheng SW, Cheng YJ, Hsu CS (2015) Donor–acceptor conjugated polymers based on multifused ladder-type arenes for organic solar cells. Chem Soc Rev 44:1113–1154

Fernandes SSM, Castro MCR, Ivanou D, Mendes A (2022) Push-pull heterocyclic dyes based on pyrrole and thiophene: synthesis and evaluation of their optical. Redox Photovoltaic Prop Coatings 12:34

Ahluwalia G, Subbiah J, Mitchel VD, Neto NS, Jones DJ (2022) One-pot synthesis of fully conjugated amphiphilic block copolymers using asymmetrically functionalized push-pull monomers. Macromol 55:2872–2881

Marinelli M et al (2022) Ionic push-pull polythiophenes: a further step towards eco-friendly BHJ organic solar cells. Polymers 14:3965

Malytskyi V, Simon JJ, Patrone L, Raimundo JM (2015) Thiophene-based push-pull chromophores for small molecule organic solar cells (SMOSCs). RSC Adv 5:354–397

Castro MCR, Belsley M, Raposo MMM (2016) Push-pull second harmonic generation chromophores bearing pyrrole and thiazole heterocycles functionalized with several acceptor moieties: Syntheses and characterization. Dyes Pigms 128:89–95

Fernandes SSM et al (2017) Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push-pull organic dyes with different anchoring groups for dye-sensitized solar cells. ACS Omega 2:9268–9279

Lim HC et al (2020) Effect of a π-linker of push–pull D–π–A donor molecules on the performance of organic photodetectors. J Mater Chem C 8:11145–11152

Chang CY, Shin YH, Chen WC, Cheng CC (2022) Influence of side-chain substitution for thiophene-based conjugated polymers on the charge transport properties: Carboxylate ester group versus carboxamide group. Org Electron 110:106634

De Oliveira MA, Pernaut JM, Duarte HA, De Almeida WD (2000) Energy gaps of α, α‘-substituted oligothiophenes from semiempirical, ab initio, and density functional methods. J Phys Chem A 104:8256–8262

Zheng C, Pan J, Chen R, Wang W, Huang W (2014) Theoretical investigation of substitution and end-group effects on poly(p-phenylene vinylene)s. Sci China Chem 57:435–441

Santos ES, Reis VS, Guimarães L, Nascimento CS Jr (2019) Molecular wires formed from native and push-pull derivatives polypyrroles and β-cyclodextrin: A HOMO-LUMO gap theoretical investigation. Chem Phys Lett 730:141–146

Coleone AP, Lascane LG, Batagin-Neto A (2019) Polypyrrole derivatives for optoelectronic applications: a DFT study on the influence of side groups. Phys Chem Chem Phys 21:17729–17739

Paulino PHS, Silva CF, De Almeida WB, Guimarães L, Nascimento CS Jr (2021) A theoretical study of poly(p-phenylenes) and their cyclodextrin-based insulated molecular wires. Comput Theor Chem 1197:113157

Haroon M, Al-Saadi AA, Janjua MRSA (2022) Insights into end-capped modifications effect on the photovoltaic and optoelectronic properties of S-shaped fullerene-free acceptor molecules: A density functional theory computational study for organic solar cells. J Phys Org Chem 35:e4314

Haroon M, Janjua MRSA (2022) Exploring the effect of end-capped modification of carbazole-based fullerene-free acceptor molecules for high-performance indoor organic solar cell applications. J Comput Electon 21:40–51

Kar P (2013) Doping in Conjugated Polymers, 1st edn. John Wiley and Sons Inc, Hoboken, New Jersey, pp 20–31

Lüssem B, Riede M, Leo K (2013) Doping of organic semiconductors. Phys Status Solidi A 210:9–43

Tietze ML et al (2018) Elementary Steps in Electrical Doping of Organic Semiconductors. Nat Commun 9:1182–1190

Zhao W, Ding J, Zou Y, Di CA, Zhu D (2020) Chemical Doping of Organic Semiconductors for Thermoelectric Applications. Chem Soc Rev 49:7210–7228

Fernandes MR, Garcia JR, Schultz MS, Nart FC (2005) Polaron and bipolaron transitions in doped poly(p-phenylene vinylene) films. Thin Solid Films 474:279–284

Kroon R, Kiefer D, Stegerer D, Yu L, Sommer M, Müller C (2017) Polar side chains enhance processability, electrical conductivity, and thermal stability of a molecularly p-doped polythiophene. Adv Mater 29:1700930

Yamashita Y, Tsurumi J, Ohno M, Fujimoto R, Kumagai S, Kurosawa T, Okamoto T, Takeya J, Watanabe S (2019) Efficient molecular doping of polymeric semiconductors driven by anion Exchange. Nature 572:634–638

Paris M, Péres LO, Chauvet O, Froyer G (2006) Solid-state NMR study of Na versus K doping of para-phenylene oligomers. J Phys Chem B 110:743–747

Yueh KC et al (2009) Doping of conjugated polythiophenes with Alkyl silanes. Adv Funct Mater 19:1906–1911

Patel SN, Glaudell AM, Kiefer D, Chabinyc ML (2016) Increasing the thermoelectric power factor of a semiconducting polymer by doping from the vapor phase. ACS Macro Lett 5:268–272

He S, Mukaida M, Kirihara K, Lyu L, Wei Q (2018) Reversible protonic doping in Poly(3,4-Ethylenedioxythiophene). Polymers 10:1065

Yoon SE et al (2020) High efficiency doping of conjugated polymer for investigation of intercorrelation of thermoelectric effects with electrical and morphological properties. ACS Appl Mater Interfaces 12:1151–1158

Sakunpongpitiporn P, Phasuksom K, Sirivat A (2021) Tuning of PEDOT:PSS synthesis via multiple doping for enhanced electrical conductivity. Polym Int 70:1534–1543

Pineda EG, Azpeitia LA, Rodríguez-Presa MJ, Bolzán AE, Gervasi CA (2023) Benchmarking electrodes modified with bi-doped polypyrrole for sensing applications. Electrochim Acta 444:142011

Ullah H, Shah A-HA, Bilal S, Ayub K (2014) Doping and dedoping processes of polypyrrole: DFT study with hybrid functionals. J Phys Chem C 118:17819–17830

Ha NN, Cuong NT, Hung HV, Hung HM, Trung VQ (2017) Electronic properties of the polypyrrole-dopant anions ClO4- and MoO42-: a density functional theory study. J Mol Model 23:336

Sajid H, Ayub K, Mahmood T (2019) A comprehensive DFT study on the sensing abilities of cyclic oligothiophenes (nCTs). New J Chem 43:14120–14133

Ashraf A, Farooq U, Farooqi BA, Ayub K (2020) Electronic structure of polythiophene gas sensors for chlorinated analytes. J Mol Model 26:44

Jayasundara WJMJSR, Schreckenbach G (2020) Theoretical study of p- and n-doping of polythiophene- and polypyrrole-based conjugated polymers. J Phys Chem C 124:17528–17537

Alesadi A, Fatima F, Xia W, Kilin D (2021) First-principles study on the electronic properties of PDPP-based conjugated polymer via density functional theory. J Phys Chem B 125:8953–8964

Keya KN, Xia W, Kilin D (2022) DFT simulation od conductivity of the p-type doped and charge-injected cis-polyacetylene. Mol Phys e2110167. https://doi.org/10.1080/00268976.2022.2110167

Wu EC, Schwartz BJ (2023) Does the Traditional band picture describe the electronic structure of doped conjugated polymers? TD-DFT and natural transition orbital study of doped P3HT. J Chem Theory Comput 19:6761–6769

Adamo C, Barone V (1999) Toward reliable density functional methods without adjustable parameters: The PBE0 model. J Chem Phys 110:6158–6170

Fernandes SMM et al (2017) Synthesis and characterization of novel thieno[3,2-b]thiophene based metal-free organic dyes with different heteroaromatic donor moieties as sensitizers for dye-sensitized solar cells. Dyes Pigms 136:46–53

Fernandes SMM et al (2017) Synthesis and characterization of push-pull bithiophene and thieno [3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells. Org Electron 49:194–205

Fernandes SSM et al (2018) Push-pull N, N-diphenylhydrazones bearing bithiophene or thienothiophene spacers as nonlinear optical second harmonic generators and as photosensitizers for nanocrystalline TiO2 Dye-sensitized solar cells. ACS Omega 3:12893–12904

Garza AJ, Scuseria GE (2016) Predicting band gaps with hybrid density functionals. J Phys Chem Lett 7:4165–4170

Balakirev DO et al (2022) Luminescent push-pull triphenylamine-based molecules end-capped with various electron-withdrawing groups: Synthesis and properties. Dyes Pigms 208:110777

Mawad D et al (2016) Electroconductive hydrogel based on functional poly(ethylenedioxy thiophene). Chem Mater 28:6080–6088

Choeichom P, Sirivat A (2018) Tuning poly(p-phenylene) nano-size for enhancing electrical conductivity based on surfactant templates and doping. Curr Appl Phys 18:686–697

Hua F et al (2023) Long-life P-type co-doped polyaniline cathodes for ultrahigh-energy-density aqueous zinc-ion batteries. J Energy Storage 68:107779

Frisch MJ et al (2009) Gaussian 09, Revision D.01. Gaussian, Inc., Wallingford CT

Mahmood A et al (2015) Effect of thiophene rings on UV/visible spectra and non-linear optical (NLO) properties of triphenylamine based dyes: a quantum chemical perspective. J Phys Org Chem 28:418–422

Mahmood A (2019) Photovoltaic and charge transport behavior of diketopyrrolopyrrole based compounds with A-D-A-D-A skeleton. J Clust Sci 30:1123–1130

Mahmood A, Irfan A (2020) Computational analysis to understand the performance difference between two small-molecule acceptors differing in their terminal electon-deficient group. J Comput Electon 19:931–939

Miao MS, Vam Camp PE, Van Doren VE, Ladik JJ, Mintmire JW (1998) First-principles calculation of the conformation and electronic structure of polyparaphenylene. J Phys Chem 109:9623–9631

Talipov MR, Boddeda A, Timerghazin QK, Rathore R (2014) Key role of end-capping group in optoelectronic properties of poly-p-phenylene cation radicals. J Phys Chem C 118:21400–21408

Rayne S, Forest K (2016) Benchmarking semiempirical, Hartree-Fock, DFT, and MP2 methods against the ionization energies and electron affinities of short-through long chain [n] acenes and [n] phenacenes. Can J Chem 94:251–258