Synthesis and solvatochromic behavior of branched oligophenylenes with hydroxy groups

Yamaguchi, Isao; Sato, Katsuhiko; Okuno, Masayoshi

doi:10.1002/poc.3309

Cited by 7 publications

(2 citation statements)

References 13 publications

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“…1,3,5-Tris(4-hydroxyphenyl)benzene (THPB) and [1,1′:4′,1″:4″,1‴-quaterphenyl]-4,4‴-diol (DHQP) were synthesized by applying methods reported previously. 38,39 ■ ASSOCIATED CONTENT * S Supporting Information…”

Section: ■ Conclusionmentioning

confidence: 99%

Surface-Controlled Mono/Diselective ortho C–H Bond Activation

et al. 2016

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One of the most charming and challenging topics in organic chemistry is the selective C-H bond activation. The difficulty arises not only from the relatively large bond-dissociation enthalpy, but also from the poor reaction selectivity. In this work, Au(111) and Ag(111) surfaces were used to address ortho C-H functionalization and ortho-ortho couplings of phenol derivatives. More importantly, the competition between dehydrogenation and deoxygenation drove the diversity of reaction pathways of phenols on surfaces, that is, diselective ortho C-H bond activation on Au(111) surfaces and monoselective ortho C-H bond activation on Ag(111) surfaces. The mechanism of this unprecedented phenomenon was extensively explored by scanning tunneling microscopy, density function theory, and X-ray photoelectron spectroscopy. Our findings provide new pathways for surface-assisted organic synthesis via the mono/diselective C-H bond activation.

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Section: ■ Conclusionmentioning

confidence: 99%

Surface-Controlled Mono/Diselective ortho C–H Bond Activation

et al. 2016

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“…This shift seems to be ascribed to the charge transfer from the N – anions generated via the deprotonation of the imidazole rings to the oligomer backbone. It has been reported that the deprotonation of OH group(s) of the aromatic compounds by NaH causes charge transfer from the O – anion to the inner aromatic rings, accompanied by a bathochromic shift of λ max . − …”

Section: Resultsmentioning

confidence: 99%

Ru-Complex-Catalyzed Synthesis of Telechelic Oligobenzimidazoles and Their Chemical Properties, Reactivity, and Structures

Yamaguchi

Imoto

2017

Macromolecules

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The reaction of 3,3′-diaminobenzidine (DAB) with 1,4-benzenedimethanol (BDM) in the presence of a RuCl 2 (PPh 3 ) 3 catalyst yielded oligobenzimidazoles (OBIs) with OH groups at both ends. The degrees of oligomerization (DO) of the OBIs depended on the monomer feed ratio and reaction temperature. The reaction of the OBIs with CH 3 (CH 2 ) m I (m = 0, 3, 5, 7, and 9) assisted by KOH caused both N-and O-alkylation, yielding alkylated OBI-(CH 2 ) m CH 3 . The UV−vis measurements suggest that OBI-CH 3 forms a 1:2 charge transfer complex with 7,7,8,8-tetracyanoquinodimethane (TCNQ). The intensity of OBI-CH 3 photoluminescence decreased depending on the amount of TCNQ added to the solution. The quenching behavior was investigated by Stern− Volmer analysis. The OBIs and OBI-Rs were electrochemically oxidized and reduced. The powder X-ray diffraction patterns suggest that the OBI-Rs self-assemble into ordered structures in the solid state.

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Palladium/Copper Dual Catalysis for the Cross‐Coupling of Aryl(trialkyl)silanes with Aryl Bromides

et al. 2018

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Whereas aryl(trialkyl)silanes are considered to be ideal organometallic reagents for cross-coupling reactions owingt ot heir stability,l ow toxicity,s olubility,a nd easy accessibility,t hey are generally inert under typical crosscoupling conditions.D isclosed herein is ap alladium/copper catalytic system that enables the cross-coupling of trimethyl, triethyl, tert-butyldimethyl, and triisopropyl aryl silanes with aryl bromides.This process is applicable to the sequential C À H and CÀSi bond arylation of thiophenes and the synthesis of poly(thiophene-fluorene)s.

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Synthesis and solvatochromic behavior of branched oligophenylenes with hydroxy groups

Cited by 7 publications

References 13 publications

Surface-Controlled Mono/Diselective ortho C–H Bond Activation

Surface-Controlled Mono/Diselective ortho C–H Bond Activation

Ru-Complex-Catalyzed Synthesis of Telechelic Oligobenzimidazoles and Their Chemical Properties, Reactivity, and Structures

Palladium/Copper Dual Catalysis for the Cross‐Coupling of Aryl(trialkyl)silanes with Aryl Bromides

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