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A Rational Synthetic Approach to 2,5‐Diphenyl‐β‐silyl Phospholes
Author(s) -
Klintuch Dieter,
Krekić Kristijan,
Bruhn Clemens,
Benkő Zoltán,
Pietschnig Rudolf
Publication year - 2016
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201500874
Subject(s) - silylation , chemistry , phosphole , reactivity (psychology) , lithium (medication) , chalcogen , stereochemistry , crystallography , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology , endocrinology
Systematic access to β‐silyl‐substituted phospholes is reported. The synthesis proceeds through the addition of lithium phosphanide to a diyne and silylation of the intermediate β‐lithio phosphole. By following this approach, mono and disilylation has been accomplished and the reactivity of the β‐silyl phospholes towards oxidation with chalcogens and conversion into phospholides has been explored. The silyl units have a significant impact on the fluorescence properties of the phosphole system, leading to increased Stokes shifts and blueshifted absorption with redshifted emission. The key compounds have been characterized by multinuclear NMR spectroscopy, mass spectrometry, and, in part, by single‐crystal X‐ray diffraction analysis.