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π‐Extended Indenofluorenes
Author(s) -
Rao M. Rajeswara,
Desmecht Antonin,
Perepichka Dmitrii F.
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.201406646
Subject(s) - anthracene , structural isomer , naphthalene , chemistry , regioselectivity , intramolecular force , cyclic voltammetry , ring (chemistry) , absorption (acoustics) , absorption spectroscopy , steric effects , photochemistry , quantum yield , materials science , stereochemistry , catalysis , organic chemistry , fluorescence , electrode , physics , electrochemistry , composite material , quantum mechanics
Abstract A series of π‐extended aromatic indenofluorene (IF) analogues with naphthalene and anthracene cores have been synthesized through acid‐catalyzed intramolecular cyclization. The regioselectivity of the reaction is controlled by a combination of steric and electronic factors and in some cases several possible regioisomers have resulted from the same precursor. The effects of ring connectivity on the optoelectronic properties were investigated by DFT calculations, absorption/emission spectroscopy, cyclic voltammetry, and spectroelectrochemical studies. All regioisomers exhibited a redshift of their absorption/emission bands relative to the parent IF analogues, but the magnitude of this shift and other optoelectronic properties (luminescence quantum yield, etc.) depends on the ring connectivity in a less obvious manner.