ABSTRACT:The preferred conformation of aminophosphanes with bulky amino groups (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20) was determined by NMR spectroscopy in solution, in two cases in the solid state (11,17) Ph (14), R = Bu, R = Ph (15),
and in one case (11) by X-ray crystallography. Trimethylsilylaminodiphenylphosphanes Ph 2 PN(R)SiMe 3 (R = Bu (1), Ph (2), 2-pyridyl (3), 2-pyrimidyl (4), Me 3 Si (5)), amino-(chloro)phenylphosphanes Ph(Cl)PNRR (R
Lithiation of 2-(2-bromophenyl)-dioxolane (1) followed by reaction with dimesitylboron fluoride afforded 2-(2-dimesitylborylphenyl)-dioxolane (2) which was deprotected to afford 2-dimesitylboryl-benzaldehyde (3). Compound 3 reacts with aliphatic amines such as n-butylamine and ethanolamine to afford the corresponding imines 2-(dimesitylboryl)benzylidenebutylamine (4) and 2-(dimesitylboryl)benzylideneethanolamine (5), respectively. Structural studies indicate coordination of the imine-nitrogen atom to the boron center. Imines 4 and 5 emit a green fluorescence near 510 nm with quantum yields approaching 10 %. TD-DFT calculations suggest that this emission arises from an intramolecular charge-transfer excited state.
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