The
development of efficient methods for the synthesis of substituted
polycyclic arenes with various topologies is in high demand due to
their excellent electrical and optical properties. In this work, a
series of gem-dimethylcyclopentane-fused arenes with
more than ten topologies were synthesized via a 1,5,7-Triazabicyclo[4.4.0]dec-5-ene
(TBD)-mediated dehydro-Diels–Alder reaction with moderate to
good yields. The introduction of the near-planar gem-dimethylcyclopentane moiety not only impacts the molecular conjugative
system but also regulates the intermolecular π–π
interactions and crystal packing, which are critical for the photoelectric
performance of arenes. The photophysical properties, molecular geometry,
molecular packing of these compounds, and electrochemical properties
were investigated by UV–vis absorption, fluorescence emission
spectra, DFT calculations, single-crystal X-ray structure analysis,
and cyclic voltammetry study.
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