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

Organic crystalline materials having a lamellar pi-pi 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 pi-pi stacked crystalline materials with a interplanar pi-pi distance of 3.247 angstrom, more than 0.1 angstrom shorter than that of highly oriented pyrolytic graphite (HOPG) where interplanar distance ranges from 3.35 to 3.39 angstrom.