Heteroannulated acceptors based on benzothiadiazole

Parker, Timothy C.; Patel, Dinesh G.; Moudgil, Karttikay; Barlow, Stephen; Risko, Chad; Brédas, Jean Luc; Reynolds, John R.; Marder, Seth R.

doi:10.1039/c4mh00102h

Cited by 130 publications

(114 citation statements)

References 156 publications

(180 reference statements)

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“…273,274,290,291,298,303312,320,321,323,325334 Still it is taken for granted that they should be utilized in the form of nothing but thin films. Considering the high efficiency of photoconduction, the salts discussed in this account or related compounds may include materials of choice for photovoltaic cells utilized as single crystals with the aid of optical doping.…”

Section: Resultsmentioning

confidence: 99%

Development of a Control Method for Conduction and Magnetism in Molecular Crystals

Naito

2016

Bulletin of the Chemical Society of Japan

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This study concerns development of a non-destructive method to control conduction and magnetism of molecular solids such as single crystals of charge-transfer complexes. The method is named “optical doping”, where appropriate irradiation is utilized under ambient conditions. Owing to this feature, it can be applied to a wide range of substances while measuring the properties during the control. In addition, the method adds unique conduction and magnetic properties to common insulators. Unlike other doping methods, optical doping only affects the properties and/or structures of the irradiated part of a sample while leaving the rest of the sample unchanged. There are two patterns in the optical doping. Irreversible optical doping produces junction-structures on the single molecular crystals, which exhibit characteristic behavior of semiconductor devices such as diodes and varistors. Reversible optical doping produces “giant photoconductors” and “photomagnetic conductors” by realizing unprecedented metallic photoconduction. In the latter case, localized spins are also excited to produce a Kondo system, where carriers and localized spins interact with each other. Not only the control of conduction and magnetism, the optical doping has realized the observation of physical properties in molecular crystals hardly observed under any thermodynamic condition.

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Section: Resultsmentioning

confidence: 99%

Development of a Control Method for Conduction and Magnetism in Molecular Crystals

Naito

2016

Bulletin of the Chemical Society of Japan

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“…Recently, many efforts have been devoted to developing effective and easy-to-handle dopant molecules with suitable HOMO/LUMO levels for organic electronic materials. 1, 2, 7, 9–13 Understanding the doping mechanism between dopant and host molecules is crucial for utilizing the doping process in a more efficient and controllable manner. The doping of poly(3-hexylthiophene) (P3HT) by 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F 4 -TCNQ) is one of the most extensively studied p-doping systems in both solution and thin film forms.…”

Section: Introductionmentioning

confidence: 99%

The impact of aggregation on the p-doping kinetics of poly(3-hexylthiophene)

et al. 2017

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The morphological effects of regioregular poly(3-hexylthiophene) (P3HT) on its p-doping kinetics with 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ) in solution are studied using optical absorption spectroscopy and stopped-flow technique. Two morphological forms, solubilized (s-P3HT) and nanowhiskers (nw-P3HT), are investigated. Both P3HT solubilized and aggregated solutions show similar characteristic near-IR absorption bands for integer charge transfer products with F4-TCNQ. Kinetic analysis on p-doping of s-P3HT with F4-TCNQ indicates that the doping reaction proceeds with a single reaction mechanism that is first order in s-P3HT. The doping kinetics of P3HT aggregate solution shows two distinctive reaction mechanisms. The slow mechanism has a reaction rate constant similar to that of solubilized P3HT solution, so it likely results from s-P3HT components that are present in the aggregate solution. The fast one is assigned to the nw-P3HT component, probably due to more efficient charge delocalization in the aggregated P3HT nanostructures. Additionally, the kinetic trends of the p-doping reactions are better fitted with the consideration of a Gaussian-like distribution of reactivities from P3HT, matching the complexity of polymeric systems originating from molecular weight and morphology variations. This study highlights the importance of considering different morphological forms of conjugated polymers on their charge-transfer reaction kinetics. The knowledge gained here should be fundamentally and practically important for future chemical doping applications in organic electronic device fabrications.

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“…Electrochemical measurements are consistent with a reduction in both the HOMO-LUMO energies (E HOMO = −5.10 eV; E LUMO = −3.95 eV; E elec g of 1.15 eV). Heteroannulated variants of BT, such as thiadiazoloquinoxaline (TQ) result in a significant reduction in the LUMO, 20 which can be mitigated by the presence of thiophene spacers. To demonstrate the ultimate utility of copolymers based on CvCPh substitution, BHJ photodetectors were fabricated using P2-P5 in combination with [70]PCBM.…”

Section: Polymer Chemistry Papermentioning

confidence: 99%