Gram-Scale Synthesis and Supramolecular Complex of Precursors of Clar’s Hydrocarbon Triangulene
Author(s) -
Peter Ribar,
Tomáš Šolomek,
Michal Jurı́ček
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b02683
Subject(s) - chemistry , supramolecular chemistry , hydrocarbon , cyclophane , solid state , gram , core (optical fiber) , crystallography , scale (ratio) , combinatorial chemistry , stereochemistry , crystal structure , organic chemistry , materials science , physics , quantum mechanics , biology , bacteria , composite material , genetics
We present to date the most efficient gram-scale synthesis of triangulene-4,8-dione and 12-hydroxytriangulene-4,8-dione, the precursors of Clar's hydrocarbon, in overall yields >50%. The direct dihydroprecursors of triangulene, obtained upon reduction of triangulene-4,8-dione, were stabilized in a supramolecular complex with a tetracationic cyclophane ExBox 4+ and characterized by single-crystal X-ray crystallography. This result represents the first step in an endeavor to stabilize the fragile core of triangulene in an inclusion complex in solution and solid state.
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