Rational Design of Lamellar π–π Stacked Organic Crystalline Materials with Short Interplanar Distance

Organic
crystalline materials having a lamellar π–π
stacked structural motif with short interplanar distance are significant
for many applications. By asymmetrically introducing perfluoroalkyl
substituents onto and polarizable sulfur atoms into N-containing heteroaromatics,
we successfully synthesized a novel type of aromatic material that
preferentially forms lamellar π–π stacked crystalline
materials with a interplanar π–π distance of 3.247
Å, more than 0.1 Å shorter than that of highly oriented
pyrolytic graphite (HOPG) where interplanar distance ranges from 3.35
to 3.39 Å.