Open AccessHelically Arranged Chiral Molecular Nanographenes
Author(s) -
Patricia IzquierdoGarcía,
Jesús M. FernándezGarcía,
Israel Fernández,
Josefina Perles,
Nazario Martín
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c05977
Subject(s) - chemistry , enantiomer , diastereomer , covalent bond , chirality (physics) , isomerization , crystallography , stereochemistry , fluorescence , racemic mixture , molecule , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , catalysis
A benchtop solution-phase synthesis of molecular nanographenes composed of two orthogonal dibenzo[fg,ij]phenanthro[9,10,1,2,3-pqrst]pentaphene (DBPP) moieties covalently connected through a tetrafluorobenzene ring is described. The helical arrangement of these three covalently linked molecular fragments leads to the existence of a chiral axis which gives rise to a racemic mixture, even with the molecular moieties being symmetrically substituted. X-ray diffraction studies show that both enantiomers cocrystallize in a single crystal, and the racemic mixture can be resolved by chiral HPLC. Asymmetric substitution in DBPP moieties affords a pair of diastereoisomers whose rotational isomerization has been studied by 1 H NMR. Additionally, the electrochemical and photophysical properties derived from these new molecular nanographenes reveal an electroactive character and a significant fluorescent behavior.