Perfluorophenyl derivatives of the elements VIII. Unstable organometallic intermediates in the synthesis of polyhaloaromatic compounds

Cohen, S.C.; Fenton, David E.; Tomlinson, A. J.; Massey, Andrew

doi:10.1016/s0022-328x(00)81508-9

Cited by 35 publications

(5 citation statements)

References 7 publications

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“…114 Of note for this current review, the stannafluorenes (109 and 110; Scheme 8) were prepared according to a general procedure developed previously by Cohen and coworkers. 115,116 While compound 109 was non-emissive, placement of phenylethynyl (-CRCPh) substituents at the 2-and 7-positions of the stannafluorene ring (to give 110) resulted in a red-shift in the absorption from 309 nm in 109 to 350 and 363 nm for 110, consistent with an increase in the extent of conjugation. In addition compound 110 yields blue-colored fluorescence both in solution (THF: l em = 389 and 410 nm) and in the solid state (l em = 485 nm).…”

Section: Tinmentioning

confidence: 99%

Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications

2016

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This review article summarizes recent progress in the synthesis and optoelectronic properties of conjugated materials containing heavy main group elements from Group 13-16 as integral components. As will be discussed, the introduction of these elements can promote novel phosphorescent behavior and support desirable molecular and polymeric properties such as low optical band gaps and high charge mobilities for photovoltaic and thin film transistor applications.

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Section: Tinmentioning

confidence: 99%

Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications

2016

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“…During this work, we also attempted the transmetallation of alkylzinc halides with mercuric chloride [7*], and observed a very incomplete reaction. However, upon treating a THF suspension of MercUrow chloride [8] Hg,Cl, (1 equiv.) cooled to -50°C with a THF solution of an organozinc reagent [3] FG-RZnI 11 (2.5 equiv.)…”

mentioning

confidence: 99%

Preparation of polyfunctional diorganomercurials and their transmetallation to diorganozincs. Applications to the preparation of optically active secon

Rozema

Duddu

Tucker

et al. 1992

Journal of Organometallic Chemistry

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Two new methods of preparation of functionalized diorganomercurials have been developed. The first method involves a substitution reaction of (ICH,),Hg with zinc-copper reagents FG-RCu(CN)ZnI in THF/DMF at-60°C. Functional groups such as an ester, nitrile, ketone, phosphonate, halide, and boronic ester are tolerated in this reaction. The second method involves a reductive transmetallation between poly-functional organozinc halides and mercurous chloride (Hg,CI,). This very convenient procedure provides a rapid route to various functionalized diorganomercurials in good yields (61-89% yield). The synthetic utility of these mercury organometallics is demonstrated. Their transmetallation with zinc dust (toluene, 8o"C, 3-5 h) affords dialkylzincs which add enantioselectively to aldehydes in the presence of a catalytic amount 120 mol%) of the norephedrine derivative 13. This transmetallation can also be used to prepare stereoselectively (E)-alkenylzinc halides (> 98% El. Addition of CI(H)ZrCp, to (E)-S-chloropentenylzinc bromide in CH,Cl, (2S"C, 1 min) affords a l,l-bimetallic of zinc and zirconium CI(CH,),CH(ZnBr)ZrCp,(CI) which reacts stereoselectively with an aldehyde providing the (Ebdisubstituted olefin (49% yield; 100% El.

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“…2-Bromo-2′-hexyl-5,5′-bithiophene was prepared by bromination of (5-hexyl-2,2′-bithiophene) with NBS. 2,2′-Dibromooctafluorobiphenyl, 2-bromo-3-hexyl-thiophene, and 3,3′′′-dihexyl-2,2′,2′′,2′′′,5′,5′′-tetrathiophene , were prepared as described in the literature.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of Fluorinated Heterofluorene-Containing Donor−Acceptor Systems

Geramita¹,

Tao²,

Segalman³

et al. 2010

J. Org. Chem.

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A series of oligothiophene-perfluoro-9-heterofluorene donor-acceptor (DA) compounds was synthesized via a combination of nucleophilic aromatic substitution (S(N)Ar(F)) and palladium coupling reactions. These compounds are of interest as possible building blocks for materials with useful electron transport properties, since they possess relatively low LUMO energy levels of -3.3 to -3.6 eV (as determined by differential pulse voltammetry). The HOMO-LUMO energy gaps, as determined by UV-vis spectroscopy, range between 2.4 and 2.5 eV, and photoluminescence emission spectra reveal lambda(ems) values in the range of 480-600 nm (corresponding to yellow-orange emission). Dilute solution-state photoluminescence quantum yields were significantly lower than those of the pure acceptor heterofluorenes (0.02-0.38 for the DA compounds vs approximately 1 for the pure acceptors), and notable solvatochromism in the fluorescence suggests emission from a charge-separated state. Theoretical calculations show that HOMO-level electron density is more localized on the thiophene fragment, while the LUMO level electron density is mostly associated with the electron-deficient portion of the molecule. Photovoltaic (PV) devices based on DA/poly-3-hexylthiophene (P3HT) blends exhibit improved performance over P3HT-only devices, suggesting the ability of these DA compounds to transport electrons in the solid state.

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Perfluorophenyl derivatives of the elements VIII. Unstable organometallic intermediates in the synthesis of polyhaloaromatic compounds

Cited by 35 publications

References 7 publications

Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications

Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications

Preparation of polyfunctional diorganomercurials and their transmetallation to diorganozincs. Applications to the preparation of optically active secon

Synthesis and Characterization of Fluorinated Heterofluorene-Containing Donor−Acceptor Systems

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