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Preparation of Tetrabenzo[4.4.2]undecastarphene by On‐Surface Synthesis
Author(s) -
Jancarik Andrej,
Khanh Hung Nguyen,
Skidin Dmitry,
Moresco Francesca,
Gourdon Andre
Publication year - 2021
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202100112
Subject(s) - molecule , chemistry , annealing (glass) , yield (engineering) , conformational isomerism , carbon fibers , crystallography , stereochemistry , organic chemistry , materials science , composite number , metallurgy , composite material
Abstract A large dissymmetric starphene molecule, the tetrabenzo[ a , c , u , w ]naphtho[2,3‐ l ]nonaphene, was obtained by first preparing a soluble precursor which was then sublimated on a Au(111) surface in an ultra‐high vacuum. In a second step, controlled annealings from 200 °C to 275 °C initiated two successive cyclodehydrogenation steps with the formation of 3 new carbon‐carbon bonds. A second conformer was also stable enough during the annealing step to give another compound in similar yield, the benzodibenzo[7,8,9,10]naphthaceno[2,1‐ h ]phenanthro[9,10‐ p ]hexaphene. The formation of this more‐hindered species stresses the importance of strong molecule‐surface interactions during the cyclodehydrogenations steps of these large polyaromatic hydrocarbons.