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Isomerically Pure Star‐Shaped Triphenylene–Perylene Hybrids Involving Highly Extended π‐Conjugation
Author(s) -
Nuin Edurne,
Lloret Vicent,
Amsharov Konstantin,
Hauke Frank,
Abellán Gonzalo,
Hirsch Andreas
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.201705872
Subject(s) - triphenylene , perylene , supramolecular chemistry , chromophore , molecule , raman spectroscopy , conjugated system , coronene , chemistry , regioselectivity , surface modification , porphyrin , materials science , combinatorial chemistry , photochemistry , organic chemistry , polymer , catalysis , physics , optics
The synthesis and characterization of a new type of a highly conjugated heterocyclic π‐chromophore, consisting of a central triphenylene core fused with three perylene monoimide units (star‐shaped molecules), is described. By judicious bay functionalization with tert ‐butylphenoxy substituents, aggregation was completely prevented by using 1,1,2,2‐tetrachloroethane, allowing for a straightforward purification and, for the very first time, the complete separation of the constitutional isomers by HPLC. Both isomers can be easily distinguished by means of several conventional spectroscopic techniques. Furthermore, we have illustrated the absence of supramolecular aggregates and enhanced processability by noncovalent functionalization of graphene substrates, showing an outstanding homogeneity and demonstrating a different doping behavior in both isomers, making it possible to distinguish them by Raman spectroscopy.