Fabrication of Organic Single Crystal Transistors Based on 5,9-Diphenyldinaphtho[2,1-b:1’,2’-d]furan Derivatives

Kunugi, Yoshihito; Maeda, Ayami; Arakawa, Teppei; Okamoto, Kazuo

doi:10.2494/photopolymer.27.317

Cited by 2 publications

(2 citation statements)

References 13 publications

(12 reference statements)

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“…[Mechanism #1] (Figure 4-(a)) The introduction of bromine atoms on 5-and 9-positions of DNF could generate a large steric repulsion with peri-position hydrogens H 4 and H 10 , respectively, and H 4 and H 10 were pushed in the H 3 and H 11 directions, respectively. Similarly, H 3 and H 11 could push H 2 and H 12 , respectively. Of course, the positions of the carbon back-Table 1.…”

Section: Structural Optimization and Remote Steric Effectmentioning

confidence: 99%

Remote Steric Effect Propagation through Naphthalene Hydrogens and/or Molecular Skeleton: Structural Determination of Brominated Product of Dinaphtho[2,1‐b:1′,2′‐d]furan

et al. 2022

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We performed a bromination reaction of dinaphtho[2,1‐b:1′,2′‐d]furan (DNF). Although similar reactions have been reported, the regioselectivity of this reaction has not been clarified. Single‐crystal diffraction study confirmed that two bromine atoms were introduced on 5‐ and 9‐positions of DNF. Detailed studies revealed that the steric effect of the bulky bromine atoms propagated through the peripheral hydrogens and/or the skeleton of DNF to result in the large helicity. This structural characteristic became apparent from the shift of the signals of Fjord hydrogens in the 1H NMR spectra. Theoretical studies also supported our proposed remote steric effect.

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Section: Structural Optimization and Remote Steric Effectmentioning

confidence: 99%

Remote Steric Effect Propagation through Naphthalene Hydrogens and/or Molecular Skeleton: Structural Determination of Brominated Product of Dinaphtho[2,1‐b:1′,2′‐d]furan

et al. 2022

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“…Other chemicals were purchased and used without further purification. The three-step synthetic route to O5H- Areephong et al, 2004]) and 5,9dibromodinaphtho[2,1-b:1',2'-d]furan (Br-O5H [Kunugi et al, 2014]) were synthesized according to the reported procedures in the yields of 95% and 98%, respectively, and identified by 1 H NMR spectra. N 5 ,N 5 ,N 9 ,N 9 -tetrakis(4-methoxyphenyl)dinaphtho[2,1-b:1',2'd]furan-5,9-diamine (O5H-OMeDPA) was prepared as follows: to a three-neck round bottom flask were added 5,9-dibromodinaphtho[2,1-b:1',2'-d]furan (852 mg, 2.00 mmol), 4,4′-dimethoxydiphenylamine (962 mg, 4.20 mmol), Pd2(dba)3 (91 mg, 0.10 mmol), P(t-Bu)3•HBF4 (58 mg, 0.20 mmol), NaO(t-Bu) (577 mg, 6.00 mmol), and toluene (50 mL).…”

Section: Limitations Of the Studymentioning

confidence: 99%

An Oxa[5]helicene-Based Racemic Semiconducting Glassy Film for Photothermally Stable Perovskite Solar Cells

Yang

Ricciarelli

et al. 2019

iScience

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Summary Attaining the durability of high-efficiency perovskite solar cells (PSCs) operated under concomitant light and thermal stresses is still a serious concern before large-scale application. It is crucial to maintain the phase stability of the organic hole-transporting layer for thermostable PSCs across a range of temperatures sampled during device operation. To address this issue, we propose a racemic semiconducting glassy film with remarkable morphological stability, exemplified here by a low-molecular symmetry oxa[5]helicene-centered organic semiconductor (O5H-OMeDPA). The helical configuration of O5H-OMeDPA confers the trait of multiple-dimension charge transfer to the solid, resulting in high hole mobility of 6.7 × 10 −4 cm 2 V −1 s −1 of a solution-processed glassy film. O5H-OMeDPA is combined with a triple-cation dual-halide lead perovskite to fabricate PSCs with power conversion efficiencies of 21.03%, outperforming the control cells with spiro-OMeTAD (20.44%). Moreover, the cells using O5H-OMeDPA exhibit good long-term stability during full-sunlight soaking at 60°C.

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Fabrication of Organic Single Crystal Transistors Based on 5,9-Diphenyldinaphtho[2,1-b:1’,2’-d]furan Derivatives

Cited by 2 publications

References 13 publications

Remote Steric Effect Propagation through Naphthalene Hydrogens and/or Molecular Skeleton: Structural Determination of Brominated Product of Dinaphtho[2,1‐b:1′,2′‐d]furan

Remote Steric Effect Propagation through Naphthalene Hydrogens and/or Molecular Skeleton: Structural Determination of Brominated Product of Dinaphtho[2,1‐b:1′,2′‐d]furan

An Oxa[5]helicene-Based Racemic Semiconducting Glassy Film for Photothermally Stable Perovskite Solar Cells

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