Synthesis, Structures, and Properties of BN-Dinaphthothiophenes: Influence of B and N Placement on Photophysical Properties and Aromaticity

Substitution
of the CC functionality with the isosteric
and isoelectronic B–N moiety has emerged as a powerful way
to expand the family of polycyclic aromatic hydrocarbons. In this
paper, two types of BN-dinaphthothiophene (BN-DNT) derivatives
with different B and N substitution patterns were synthesized in short
steps from commercially available materials. X-ray crystallographic
analysis revealed that BN-DNT 1 and 2 had
rigid and planar frameworks. Their photophysical properties and the
aromaticity of the BN rings of the BN-DNTs were slightly dependent on the B and N substitution
patterns. However, their response toward fluoride anions was greatly
dependent on the B and N substitution patterns.