Phosphaacene as a structural analogue of thienoacenes for organic semiconductors

Matsuo, Kyohei; Okumura, Rina; Hayashi, Hironobu; Aratani, Naoki; Jinnai, Seihou; Ie, Yutaka; Saeki, Akinori; Yamada, Hiroko

doi:10.1039/d2cc05122b

Cited by 6 publications

(3 citation statements)

References 44 publications

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“…Recently, this aromatization method was employed for synthesis of an extremely stable benzo [b]thiophene-fused phosphinine derivative. [7] π-Extension from 9-phosphaanthracene to 5-phosphatetracene II in Figure 1a should be of great interest because many ChemPlusChem www.chempluschem.org attractive and applicable physical properties of acenes have been reported so far. [8] However, it seems to be difficult to complete isolation and characterization of tetracene-like πconjugated system II because of the potent instability of acenes promoted by the potent open-shell characters.…”

Section: Introductionmentioning

confidence: 99%

“…[10] Moreover, increase of the fused benzene ring from I would promote twisting the hetero-PAH skeleton producing helical structures. Very recently, Beránek and co-workers reported a 2phospha [7]helicene which is promising as a photo-functional compound. [11] In this paper, we demonstrate a π-extension process from 9phosphaanthracene leading to 12-phosphatetraphene III and 9phosphabenzo [f]tetraphene IV by utilizing the deaminative aromatization reaction.…”

Section: Introductionmentioning

confidence: 99%

“…This deaminative aromatization is promising for π‐extending based on the 9‐phosphaanthracene platform. Recently, this aromatization method was employed for synthesis of an extremely stable benzo[ b ]thiophene‐fused phosphinine derivative [7] …”

Section: Introductionmentioning

confidence: 99%

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A π‐Extension Process from 9‐Phosphaanthracene Leading to Phosphatetraphenes and Phosphatetracenes

Yasuda

Ito

2023

ChemPlusChem

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Extension of π‐system with phosphinine (phosphorine, phosphabenzene) has been of interest because of the expected higher HOMO and lower LUMO levels compared with the corresponding carbon congeners. In this paper, a π‐extension process based on the 9‐phosphaanthracene skeleton was demonstrated by synthesizing 12‐phosphatetraphene and 9‐phosphabenzo[f]tetraphene by utilizing the deaminative aromatization pathway. Starting from 3,5‐bis(trifluoromethyl)aniline, we developed the dibromotriarylmethane precursors containing the 3,5‐bis(trifluoromethyl)‐2‐bromophenyl unit, which would be slightly effective to increase the steric congestion around the fragile P=C bonds incorporated in the fused polyaromatic skeletons. The bis‐trifluoromethyl 12‐phosphatetraphenes have been synthesized together with the mono‐trifluoromethyl derivative, and the planar 12‐phosphatetraphene skeleton was confirmed. On the other hand, the CF3‐substituted 9‐phosphabenzo[f]tetraphene displayed a remarkably twisted fused five ring system leading to the wavy structures incorporating phosphinine. Also, synthetic study of 5‐phosphatetracene using the bis(trifluoromethyl)phenyl unit was attempted and the incomplete elimination of the amine indicated labile characters of the observed phosphorus congener of tetracene. The findings of this study would be informative for developing heavier congeners of polyaromatic hydrocarbons (PAHs) as well as the trifluromethyl effects.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A π‐Extension Process from 9‐Phosphaanthracene Leading to Phosphatetraphenes and Phosphatetracenes

Yasuda

Ito

2023

ChemPlusChem

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Introduction of Phosphinine Ring into Aromatic Systems via Alkyne Cyclization

Mizerová,

Kos,

Jakubec

et al. 2024

Adv Synth Catal

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Recently developed synthetic protocols for the preparation of λ3‐phosphanaphthalenes have broadened the general scope of organophosphorus chemistry, but a versatile protocol is still missing. Here, we describe a scalable synthetic approach for the construction of various substituted phosphanaphthalenes. We have obtained 11 derivatives through rigorous study and have demonstrated the robustness of this method. The optical properties of these phosphorus compounds and their aza and carbo analogues have been experimentally compared. Here, we show the power of the method in extending the synthesis to even larger polycyclic aromatic systems with embedded phosphine rings toward its potential applicability to materials science.

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Advancement in Synthetic Strategies of Phosphorus Heterocycles: Recent Progress from Synthesis to Emerging Class of Optoelectronic Materials

Thakur,

Sushmita,

Meena

et al. 2024

The Chemical Record

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Organophosphorus heterocycles have long been acknowledged for their significant potential across diverse fields, including catalysis, material science, and drug development. Incorporating phosphorus functionalities into organic compounds offers a means to effectively tailor their medicinal properties, augment biological responses, and enhance selectivity and bioavailability. The distinctive physical and photoelectric characteristics of phosphorus‐containing conjugated compounds have garnered considerable interest as promising materials for organic optoelectronics. These compounds find extensive utility in various applications such as light‐emitting diodes, photovoltaic cells, phosphole‐based fluorophores, and semiconductors.

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Phosphaacene as a structural analogue of thienoacenes for organic semiconductors

Abstract: Air-stable λ3-phosphinine-containing polycyclic aromatic compound without steric protection was synthesized and its charge transporting property was evaluated, resulting in moderate hole mobility. This research is the first experimental demonstration of...

Cited by 6 publications

References 44 publications

A π‐Extension Process from 9‐Phosphaanthracene Leading to Phosphatetraphenes and Phosphatetracenes

A π‐Extension Process from 9‐Phosphaanthracene Leading to Phosphatetraphenes and Phosphatetracenes

Introduction of Phosphinine Ring into Aromatic Systems via Alkyne Cyclization

Advancement in Synthetic Strategies of Phosphorus Heterocycles: Recent Progress from Synthesis to Emerging Class of Optoelectronic Materials

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