Convenient Preparation of Tetraarylphosphonium Halides

Migita, Toshihiko; Nagai, Tohru; Kiuchi, Kazuhiko; Kosugi, Masanori

doi:10.1246/bcsj.56.2869

Cited by 73 publications

(34 citation statements)

References 3 publications

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“…Consequently, no phosphonium salt could be identified in the case of 10‐bromo‐9‐( N , N ‐diphenylamino)anthracene (Scheme S3), including by the modified Charette (Scheme S3, conditions b), Migita, and Heck palladium‐catalyzed syntheses (Scheme S3). As a consequence of these failures, we explored an alternative two‐step approach.…”

Section: Resultsmentioning

confidence: 99%

A Facile Molecular Machine: Optically Triggered Counterion Migration by Charge Transfer of Linear Donor‐π‐Acceptor Phosphonium Fluorophores

et al. 2019

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The D‐π‐A type phosphonium salts in which electron acceptor (A=‐+PR3) and donor (D=‐NPh2) groups are linked by polarizable π‐conjugated spacers show intense fluorescence that is classically ascribed to excited‐state intramolecular charge transfer (ICT). Unexpectedly, salts with π=‐(C6H4)n‐ and ‐(C10H6C6H4)‐ exhibit an unusual dual emission (F1 and F2 bands) in weakly polar or nonpolar solvents. Time‐resolved fluorescence studies show a successive temporal evolution from the F1 to F2 emission, which can be rationalized by an ICT‐driven counterion migration. Upon optically induced ICT, the counterions move from ‐+PR3 to ‐NPh2 and back in the ground state, thus achieving an ion‐transfer cycle. Increasing the solvent polarity makes the solvent stabilization dominant, and virtually stops the ion migration. Providing that either D or A has ionic character (by static ion‐pair stabilization), the ICT‐induced counterion migration should not be uncommon in weakly polar to nonpolar media, thereby providing a facile avenue for mimicking a photoinduced molecular machine‐like motion.

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Section: Resultsmentioning

confidence: 99%

A Facile Molecular Machine: Optically Triggered Counterion Migration by Charge Transfer of Linear Donor‐π‐Acceptor Phosphonium Fluorophores

et al. 2019

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“…Reaction of the lithiated azobenzene derivative with Ph 2 PCl or PCl 3 , respectively, leads to 5 and 6, which were subsequently quaternised with methyl iodide. Compound 3 was synthesised by a palladium(0)-catalysed reaction [18] from 5 with the iodoazobenzene derivative 4-I. All salts were purified by column chromatography and are hygroscopic crystalline solids (1) or low-melting glasses (2, 3).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Nonlinear Optical Properties of Three-Dimensional Phosphonium Ion Chromophores

et al. 1998

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Here we describe the synthesis and the linear and nonlinear optical properties of three dibutylaminoazobenzenephosphonium salt chromophores: a onedimensional system with one azobenzene subchromophore and two three-dimensional systems, one with C 3 symmetry (three subchromophores) and one with approximate T symmetry (four subchromophores). Experimental investigations (UV/Vis spectroscopy and hyper-Rayleigh scattering), theoretical calculations (exciton coupling theory and tensor transformations), as well as computational calculations (PM 3/time-dependent Hartree ± Fock) show that, while the linear optical properties of the 3 D compounds behave additively, the first-order hyperpolarisability b is distinctly enhanced in the 3 D compounds relative to the 1 D derivative.

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“…[15] Although functionalized TAP are proving to be valuable compounds with many applications in various areas, to date, there is no simple or general catalytic method for their preparation. [16] The palladium-catalyzed formation of TAP was first reported using aryl iodides [17] and, more recently, our group has extended this methodology to include aryl bromides and triflates [Eq. (1)].…”

Section: Introductionmentioning

confidence: 99%

Nickel‐Catalyzed Synthesis of Phosphonium Salts from Aryl Halides and Triphenylphosphine

Marcoux

Charette

2008

Adv Synth Catal

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An efficient method to synthesize functionalized tetraarylphosphonium salts is described. The nickel-catalyzed coupling reaction between aryl iodides, bromides, chlorides, or triflates and triphenylphosphine generates tetraarylphosphonium salts in high yields. The coupling is wide in scope and tolerates a variety of functional groups such as alcohols, amides, ketones, aldehydes, phenols, phosphines and amines.

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Convenient Preparation of Tetraarylphosphonium Halides

Abstract: Tetraarylphosphonium halides, particularly iodides, can be conveniently prepared by the Pd-catalyzed reaction of aryl halides and triarylphosphines in good yields.

Cited by 73 publications

References 3 publications

A Facile Molecular Machine: Optically Triggered Counterion Migration by Charge Transfer of Linear Donor‐π‐Acceptor Phosphonium Fluorophores

A Facile Molecular Machine: Optically Triggered Counterion Migration by Charge Transfer of Linear Donor‐π‐Acceptor Phosphonium Fluorophores

Synthesis and Nonlinear Optical Properties of Three-Dimensional Phosphonium Ion Chromophores

Nickel‐Catalyzed Synthesis of Phosphonium Salts from Aryl Halides and Triphenylphosphine

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