A Solid‐State Fluorescent Host System with a 2₁‐Helical Column Consisting of Chiral (1R,2S)‐2‐Amino‐1,2‐diphenylethanol and Fluorescent 1‐Pyrenecarboxylic Acid

Abstract

A solid-state fluorescent host system was created by self-assembly of a 2(1)-helical columnar organic fluorophore composed of (1R,2S)-2-amino-1,2-diphenylethanol and fluorescent 1-pyrenecarboxylic acid. This host system has a characteristic 2(1)-helical columnar hydrogen- and ionic-bonded network. Channel-like cavities are formed by self-assembly of this column, and various guest molecules can be included by tuning the packing of this column. Moreover, the solid-state fluorescence of this host system can change according to the included guest molecules. This occurs because of the change in the relative arrangement of the pyrene rings as they adjust to the tuning of the packing of the shared 2(1)-helical column, according to the size of the included guest molecules. Therefore, this host system can recognize slight differences in molecular size and shape.

(S)-(−)-1-Phenylethanaminium 4-(4,4-difluoro-1,3,5,7-tetramethyl-3a,4a-diaza-4-borata-s-indacen-8-yl)benzoate

“…We have found that to sense small molecules effectively, empty channels must be present in the crystal structure to allow the analyte molecules to penetrate the crystalline lattice, see: ; ; Smith & Mann (2009). For factors that could facilitate inefficient packing, see: Lancaster et al (2006); Imai et al (2007Imai et al ( , 2008; Brock et al (1991); Tominaga et al (2011). Molecules such as methanol and water have molecular volumes consistent with their possible incorporation in the void cavities, see: Buss et al (1998) For details of the synthesis, see: Tomasulo et al (2008).…”

Formation of Ternary Inclusion Crystal and Enantioseparation of Alkyl Aryl Sulfoxides by the Salt of Urea-Modified l-Phenylalanine and an Achiral Amine

“…The salts of carboxylic acids and primary amines are common supramolecular synthons for materials such as fluorescent materials, , liquid crystals, , and low-molecular-weight gelators. − Moreover, because of salt-formation reproducibility, the combination of carboxylic acids and amines is suitable for the assembly of supramolecular host systems. − …”

Solid‐State Fluorescence Changes of 2‐(4‐Cyanophenyl)‐5‐[4‐(diethylamino)phenyl]‐3H‐imidazo[4,5‐a]naphthalene upon Inclusion of Organic Solvent Molecules

“…The solidstate fluorescence of this host system changes depending on the guest molecules owing to their slight variations in molecular size and shape. [7] Therefore, an organic fluorescent host can be the most promising material for the construction of desirable solid-state fluorescent system.…”