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Reversing the Handedness of Self‐Assembled Porous Molecular Networks through the Number of Identical Chiral Centres
Author(s) -
Tahara Kazukuni,
Noguchi Aya,
Nakayama Ruri,
Ghijsens Elke,
De Feyter Steven,
Tobe Yoshito
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902565
Subject(s) - chirality (physics) , stereocenter , supramolecular chemistry , supramolecular chirality , scanning tunneling microscope , crystallography , materials science , self assembly , circular dichroism , stereochemistry , chemical physics , chemistry , nanotechnology , enantioselective synthesis , physics , organic chemistry , chiral symmetry , crystal structure , catalysis , quantum mechanics , nambu–jona lasinio model , quark
Scanning tunnelling microscope observations at the 1‐phenyloctane/graphite interface reveal how chiral structural information at the molecular level is transferred and expressed structurally at the 2D supramolecular level for a porous system. The chirality of self‐assembled molecular networks formed by chiral dehydrobenzo[12]annulene (cDBA) derivatives having three chiral chains and three achiral chains, alternatingly, is compared with those of cDBAs having six chiral chains reported previously. While for all cDBAs homochiral surfaces are formed, their handedness is not simply a reflection of the absolute configuration of the stereogenic centres. Both the number of stereogenic centres as well as the length of the achiral chains determine the supramolecular handedness, providing a deep insight into the supramolecular chirality induction mechanisms at play. Moreover, these cDBAs act to induce chirality in porous networks formed by achiral DBAs.