Bulk Heterojunction Solar Cells: The Role of Alkyl Side Chain on Nanoscale Morphology of Sulfur Over-rich Regioregular Polythiophene/Fullerene Blends

Salatelli, Elisabetta; Marinelli, Martina; Lanzi, Massimiliano; Zanelli, Alberto; Dell’Elce, Simone; Liscio, Andrea; Gazzano, Massimo; Maria, Francesca Di

doi:10.1021/acs.jpcc.7b11456

Cited by 19 publications

(19 citation statements)

References 39 publications

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“…In particular, (+)‐3,3′‐bis[( S )‐(2‐methylbutyl)sulfanyl]‐2,2′‐bithiophene T2SR* was obtained in high yield following the synthetic protocol based on MW‐assisted Suzuki–Miyaura reaction recently adopted for similar, optically inactive, derivatives 31 . By contrast, the preparation of the related oxyalkyl disubstituted bithiophene monomer T2OR* through this route was unsatisfactory.…”

Section: Resultsmentioning

confidence: 99%

“…By contrast, the preparation of the related oxyalkyl disubstituted bithiophene monomer T2OR* through this route was unsatisfactory. Moreover, despite the expected higher reactivity due to the presence of oxygen directly connected to the thiophene ring, the synthesis by oxidative coupling with BuLi/CuCl 2 31 was also inconclusive. However, (+)‐3,3′‐bis[( S )‐(2‐methylbutoxy)]‐2,2′‐bithiophene T2OR* could be obtained from TOR*Br with BuLi in the presence of Fe(acac) 3 according to the method adopted for similar derivatives, 32 although mixed with 40% of the HT regioisomer, as established by 1 H‐NMR spectroscopy (see Section 2 and Figure S2B).…”

Section: Resultsmentioning

confidence: 99%

“…The extra sulfur atom linked to each thiophene ring may in fact induce self‐aggregation via S···S interactions and weak CH···S hydrogen bonding 12–14 . The directionality of the above interactions, as well as the large polarizability of sulfur in thioether fragments, would favor the formation of highly anisotropic supramolecular systems characterized by antiplanar conformations involving reduced steric hindrance between the side chain substituents 31 even in the case of oligomeric constitution of the material.…”

Section: Resultsmentioning

confidence: 99%

“…In particular, (+)-3,3 0 -bis[(S)-(2-methylbutyl) sulfanyl]-2,2 0 -bithiophene T2SR* was obtained in high yield following the synthetic protocol based on MWassisted Suzuki-Miyaura reaction recently adopted for similar, optically inactive, derivatives. 31 By contrast, the preparation of the related oxyalkyl disubstituted bithiophene monomer T2OR* through this route was unsatisfactory. Moreover, despite the expected higher reactivity due to the presence of oxygen directly connected to the thiophene ring, the synthesis by oxidative coupling with BuLi/CuCl 2 31 was also inconclusive.…”

Section: Synthesismentioning

confidence: 99%

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Effect of regioregularity and role of heteroatom on the chiral behavior of oligo(heteroalkyl thiophene)s

et al. 2020

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Novel optically active oligothiophenes bearing electron‐donating chiral side chains have been prepared by synthetic methods suitable to achieve regioregular head‐to‐tail and head‐to‐head/tail‐to‐tail derivatives. In particular, the chiral (S)‐(2‐methyl)butyl moiety was linked at position 3 of the thiophene ring through heteroatoms, such as S or O, to evaluate its effect on the macro molecular aggregation and, consequently, on the chiroptical properties of the material in the solid state. The materials have been fully characterized and investigated by optical and chiroptical methods upon aggregation both from the solution and as cast films. Compared with the related head‐to‐tail and head‐to‐head/tail‐to‐tail poly(3‐alkyl)thiophene derivatives, with the same optically active moiety directly linked to the ring and possessing a higher polymerization degree, the chiroptical properties of the newly synthesized oligomers were significant, or even better, and provided insight into the role of intrachain–interchain interactions between the heteroatom and the thienyl sulfur atom.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

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Effect of regioregularity and role of heteroatom on the chiral behavior of oligo(heteroalkyl thiophene)s

et al. 2020

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“… 41 , 42 There is only one exception, namely, the family of CP/fullerene nanocomposites, which is applied in bulk-heterojunction solar cells. 43 , 44 In these solar cells both the CP and the fullerene are photoactive. In the current study, however, only the CP is photoactive, while the nanocarbons act as metallic conductors.…”

Section: Introductionmentioning

confidence: 99%

Photoelectrochemical Behavior of PEDOT/Nanocarbon Electrodes: Fundamentals and Structure–Property Relationships

2018

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In this study, we investigated the photoelectrochemical behavior of poly(3,4-ethylenedioxythiophene) (PEDOT)/carbon nanotube (CNT) and PEDOT/graphene nanocomposite photoelectrodes for the first time. Electrodeposition allowed control of both the composition and the morphology (as demonstrated by both transmission and scanning electron microscopy images) and also ensured an intimate contact between the PEDOT film and the nanocarbon scaffold. The effect of CNT and graphene on the photoelectrochemical behavior of the nanocomposite samples was studied by linear sweep photovoltammetry, incident photon-to-charge-carrier conversion efficiency measurements, and long-term photoelectrolysis coupled with gas-chromatographic product analysis. We demonstrated that the nanocarbon framework facilitated efficient charge carrier transport, resulting in a 4-fold increase in the measured photocurrents for the PEDOT/CNT electrode, compared to the bare PEDOT counterpart. The presented results contribute to the better understanding of the enhanced photoelectrochemical behavior of organic semiconductor/nanocarbon electrode assemblies and might encourage other researchers to study these intriguing hybrid materials further.

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Triphenylamine (TPA)‐Functionalized Structural Isomeric Polythiophenes as Dopant Free Hole‐Transporting Materials for Tin Perovskite Solar Cells

Balasaravanan,

Kuan,

Hsu

et al. 2023

Advanced Energy Materials

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A new series of triphenylamine (TPA)‐functionalized isomeric polythiophenes are developed as hole transporting materials (HTM) for inverted tin‐based perovskite solar cells (TPSCs). Bithiophene (BT) is first functionalized with two TPA (electron donor; D) at 3 and 5 positions to give two structural isomeric compounds (3BT2D and 5BT2D). The functionalized BT2Ds are then coupled with 3,3′‐bis(tetradecylthio)‐2,2′‐bithiophene (SBT‐14)/3,3′‐ditetradecyl‐2,2′‐bithiophene (BT‐14) to produce structural isomeric polythiophenes (1‐4), which are compared to conventional poly[N,N″‐bis(4‐butylphenyl)‐N,N″‐bis(phenyl)‐benzidine] (poly‐TPD) as HTMs for TPSCs. With the appropriate alignment of energy levels with regard to the perovskite layer, the TPA‐functionalized polymers‐based TPSCs exhibit enhanced operational stability and efficiency. Moreover, the long thiotetradecyl chain in SBT‐14 with intramolecular S(alkyl)∙∙∙S(thio) interactions restricts the molecular rotation and has a strong impact on the molecular solubility and wettability of the film during device fabrication. Among all the polymers studied, TPSCs fabricated with 3‐SBT‐BT2D polymer exhibit the highest hole mobility as well as the slowest charge recombination and achieve the highest power conversion efficiency of 8.6%, with great long‐term stability for the performance retaining ≈90% of its initial values for shelf storage over 4000 h, which is the best efficiency for non‐PEDOT:PSS‐based TPSCs ever reported.

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Bulk Heterojunction Solar Cells: The Role of Alkyl Side Chain on Nanoscale Morphology of Sulfur Over-rich Regioregular Polythiophene/Fullerene Blends

Cited by 19 publications

References 39 publications

Effect of regioregularity and role of heteroatom on the chiral behavior of oligo(heteroalkyl thiophene)s

Effect of regioregularity and role of heteroatom on the chiral behavior of oligo(heteroalkyl thiophene)s

Photoelectrochemical Behavior of PEDOT/Nanocarbon Electrodes: Fundamentals and Structure–Property Relationships

Triphenylamine (TPA)‐Functionalized Structural Isomeric Polythiophenes as Dopant Free Hole‐Transporting Materials for Tin Perovskite Solar Cells

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