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Yamamoto Coupling for the Synthesis of Benzophenes and Acene‐Based Cyclooctatetraenes
Author(s) -
Rüdiger Elias C.,
Koser Silke,
Rominger Frank,
Freudenberg Jan,
Bunz Uwe H. F.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801459
Subject(s) - tetracene , acene , pentacene , cyclic voltammetry , chemistry , photochemistry , materials science , crystallography , anthracene , molecule , organic chemistry , electrochemistry , electrode , thin film transistor
Two TIPS‐ethynylated dibromoacenes were used in a shotgun Yamamoto‐reaction with 1,2‐dibromobenzene or 4,5‐dibromoveratrol. Four soluble benzononaphenes/benzoundecaphenes were isolated in satisfactory yields. Examples of tetracene‐ and pentacene‐fused tetrabenzocyclooctatetraenes also isolated from this reaction are reported. All compounds were characterized by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, X‐ray crystallography as well as DFT and NICS calculations.