Synthesis of ten new diphenoxybiphenyls

Hammann, William C.; Schisla, R. M.

doi:10.1021/je60052a006

Cited by 7 publications

(2 citation statements)

References 8 publications

(10 reference statements)

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“…Therefore, we prepared 3a in three steps starting with cheap and commercially available 1-chloro-4-iodobenzene. The first step is an Ullmann coupling reaction 20 to give 4,4′-dichlorobiphenyl 1 21 in moderate yield, which is then nitrated to afford 2 22 in 95% yield. Finally, a Cadogan ring closure, 23 which is also used by Leclerc et al, gives 3a 19 in 63% yield.…”

Section: Resultsmentioning

confidence: 99%

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Localized versus Backbone Fluorescence inN-p-(Diarylboryl)phenyl-Substituted 2,7- and 3,6-Linked Polycarbazoles

Reitzenstein¹,

Lambert²

2009

Macromolecules

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The triarylborane acceptor in poly[9-((4-dimesitylboryl)-3,5-dimethylphenyl)-9H-carbazole]-3,6diyl P2 has a strong impact on the optical properties of this 3,6-linked carbazole main chain polymer and results in an enhanced fluorescence quantum yield because of a low-lying fluorescent CT state. In contrast, the same acceptor substituent does not influence the optical properties of poly[9-((4-dimesitylboryl)-3,5-dimethylphenyl)-9H-carbazole]-2,7-diyl P1. In the latter polymer, the optical properties are governed by conjugation along the carbazole backbone. This interpretation is supported by comparison with poly[9-(4-(diphenylmethyl)-phenyl)-9H-carbazole]-2,7-diyl P3, which serves as a reference polymer. Synthesis and characterization by gel permeation chromatography, NMR spectroscopy, absorption, and fluorescence measurements in solution and solid state and cyclic voltammetric measurements of the three polymers are presented.

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Section: Resultsmentioning

confidence: 99%

“…All other chemicals and reagents were used as received. Synthesis of 4,4'-dichlorobiphenyl 1, 21 4,4'dichloro-2-nitrobiphenyl 2, 22 2,7-dichlorocarbazole 3a, 19 3,6dichlorocarbazole 3b, 24 1,4-dibromo-3,5-dimethylbenzene 4a, 25,26 and 1-bromo-4-(diphenylmethyl)-benzene 4b 28 have already been reported in the literature.…”

Section: Methodsmentioning

confidence: 99%

Localized versus Backbone Fluorescence inN-p-(Diarylboryl)phenyl-Substituted 2,7- and 3,6-Linked Polycarbazoles

Reitzenstein¹,

Lambert²

2009

Macromolecules

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Cu,Ni, andPdMediated Homocoupling Reactions in Biaryl Syntheses: TheUllmann Reaction

Nelson

Crouch

2004

Organic Reactions

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The traditional Ullman reaction is the homocoupling of aromatic halides mediated by copper at elevated temperatures. Ullman first reported this reaction in 1901. Although the coupling conditions first reported are still widely used, a host of modifications have been made to these reactions. Some of these modifications include the use of activated and alternative metals, often resulting in much lower coupling temperatures. Nickel and palladium are the most utilized source of alternative metals, Periodic reviews have been published. This chapter covers the literature on copper, nickel, and palladium mediated homocoupling reactions in biaryl synthesis from 1901 to 2000. The focus of this chapter is the scope and limitation of these processes, preparation of the activated metal, and mechanism of the homocoupling process

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