The Air-Stable P-Heterocyclic Biradical for OFET Devices

Ito, Shigekazu; Ueta, Yasuhiro; Torihata, Yushi; Mikami, Kōichi

doi:10.1080/10426507.2014.980412

Cited by 6 publications

(3 citation statements)

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“…We expected that the highly electron‐donating character of the stable 1,3‐diphosphacyclobutane‐2,4‐diyl unit would be appropriate for developing innovative p‐type organic semiconductors. As predicted, a drop‐cast device fabricated using 1 functioned as a p‐type field‐effect transistor (FET) using a small gate voltage . This finding encouraged us to design novel arylmethyl‐substituted 1,3‐diphosphacyclobutane‐2,4‐diyls for FET devices.…”

Section: Introductionmentioning

confidence: 69%

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Exploration of 1-Arylmethyl-1,3-diphosphacyclobutane-2,4-diyls as Hole Transfer Materials

2016

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This paper describes the p‐type semiconductor characteristics of 1‐arylmethyl‐substituted air‐tolerant 1,3‐diphosphacyclobutane‐2,4‐diyls, focusing preliminarily on their hole transfer parameters deduced from their crystal and density functional theory (DFT) structures. 1‐(2‐Anthrylmethy)‐3‐t‐butyl‐2,4‐bis(2,4,6‐tri‐t‐butylphenyl)‐1,3‐diphosphacyclobutane‐2,4‐diyl functions as a p‐type field‐effect transistor (FET) with semiconductor parameters comparable to its benzyl‐substituted derivative. Thienylmethyl groups induced the FET response, and thus we investigated the utility of the 2‐thieno[3,2‐b]thiophenemethyl group. Critical parameters, including reorganization energies (λ), hole couplings (V), and hole hopping rates (W) were estimated based on experimental and DFT data. The benzyl and 2‐anthrylmethy groups constructed hole transfer pathways comparable to that of acenes, whereas the 2‐thieno[3,2‐b]thiophenemethyl substituent resulted in the assembly of a unique three‐dimensional network. The findings described in this study may lead to the fabrication of superior FET devices based on the chemistry of 1,3‐diphosphacyclobutane‐2,4‐diyl.

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Section: Introductionmentioning

confidence: 69%

“… Crystal structure of 1 showing (top) transverse dimers ( T 1 – T 4 ), parallel dimer ( P ), and (bottom) Longitudinal dimers ( L 1 , L 2 ) for hole transfer . The methyl groups and hydrogen atoms are omitted..…”

Section: Resultsmentioning

confidence: 99%

Exploration of 1-Arylmethyl-1,3-diphosphacyclobutane-2,4-diyls as Hole Transfer Materials

2016

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“…Thus, the diisopropylamino group, which can be introduced by employing LiN i Pr 2 instead of t BuLi in the first synthetic step, increases the electron donating properties of the sterically encumbered 1,3-diphosphacyclobutane-2,4-diyl chromophore [ E HOMO = −4.47 eV (N i Pr 2 derivative), −4.53 eV (for 122 )] and also reduces the HOMO–LUMO gap. Due to their high stability and even air tolerance, these diradicaloids were subsequently used in HF sensing ( 121 ) and show p-type semiconductor properties. ,− The C 2 P 2 diradicaloid ( 122 ) was also shown to capture muonium (Mu), yielding a metastable P-heterocyclic radical …”

Section: Main Group Based Diradical(oid)s: An Updatementioning

confidence: 96%