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The Bicyclo[1.1.1]pentane Framework—an Excellent Relay for π/σ Conjugation
Author(s) -
Gleiter Rolf,
Pfeifer KarlHeinz,
Szeimies Günter,
Bunz Uwe
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199004131
Subject(s) - pentane , bicyclic molecule , moiety , bromine , relay , chemistry , atomic orbital , molecular orbital , spectral line , computational chemistry , stereochemistry , physics , organic chemistry , molecule , quantum mechanics , power (physics) , electron
Photoelectron spectra of the bicyclo[1.1.1]pentanes 1 and 2 reveal a high degree of splitting (0.7 eV) between the π‐MOs of the ethynyl residues and the 4p orbitals of the bromine atoms, respectively. This is presumably due to strong interaction between the π systems and the σ system of the bicyclopentane framework. A similarly strong interaction has been demonstrated between the π and σ systems in 3 . These observations are of considerable interest from the standpoint of the bicyclo[1.1.1]pentyl moiety serving as a potential subunit in the construction of oligomers and for promoting energy transfer over long molecular distances.