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Fluorescent Pyrene‐Based Bis‐azole Compounds: Synthesis and Photophysical Analysis
Author(s) -
Ibáñez Susana,
Guerrero Antonio,
Poyatos Macarena,
Peris Eduardo
Publication year - 2015
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.201501179
Subject(s) - azole , pyrene , chemistry , carbene , melting point , homo/lumo , photochemistry , fluorescence , luminescence , solubility , combinatorial chemistry , computational chemistry , molecule , organic chemistry , materials science , antifungal , catalysis , medicine , physics , optoelectronics , dermatology , quantum mechanics
A rational synthetic procedure for the preparation of a series of pyrene‐based neutral and dicationic bis‐azole compounds is reported. The method allows the tailored design of pyrene‐based azoles with different substituents at the nitrogen atoms of the heterocycles, for which the relative conformation of the resulting bis‐azoles can be easily controlled. The bis‐azoliums were used for the preparation of the related diplatinum complexes by reaction with [{Pt(ppy)(μ‐Cl) 2 } 2 ] (ppy=2‐phenylpyridinate). The X‐ray molecular structure of one of the resulting compounds, a diplatinum(II) bis(N‐heterocyclic carbene) complex, is described. Studies on the photophysical properties of all new species are described. The emission of the bis‐azole‐based compounds seems to be independent of their substitution patterns, which basically indicates that physical properties such as solubility, melting point, and viscosity can be fine‐tuned while maintaining the luminescence properties. Finally, the energies associated with the HOMO and LUMO levels suggest that this family provides versatility to match the energy levels of a wide range of host materials, which is important for the preparation of organic light‐emitting devices.