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Highly Unsaturated Oligomeric Hydrocarbons: α‐(Phenylethynyl)‐ω‐phenylpoly[1,2‐phenylene(2,1‐ethynediyl)]
Author(s) -
Grubbs Robert H.,
Kratz Detlef
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260123
Subject(s) - chemistry , conjugated system , stacking , intramolecular force , ring (chemistry) , acetylene , phenylene , stereochemistry , coupling reaction , oligomer , medicinal chemistry , polymer chemistry , organic chemistry , polymer , catalysis
A new set of conjugated oligomers C 6 H 5 C…C–(1,2‐C 6 H 4 C…C) n – C 6 H 5 ( 10 ; n = 3–7) comprised of acetylene and phenyl units linked together at the 1,2 positions of the aromatic ring is introduced. The facile synthesis of these compounds is achieved through the Pd‐mediated coupling reaction of diiodo‐ and dibromobenzene with the appropriate ethynyl component. Spectroscopic data of the new compounds are discussed in light of electronic conjugation of the extended π system. Thermolysis of oligomers 10 indicates that rearrangement of the triple bonds occurs to form higher conjugated oligo(acenes). The topology of two members ( 10 ; n = 2, 3) is confirmed by X‐ray analysis and reveals a propensity for intramolecular π‐stacking of the phenyl rings leading to a helical arrangement.