title: Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid via competitive binary/ternary hydrogen-bonded complexes with 4-benzamidoprolinol.
abstract: Circular dichroism (CD) spectral examinations at various host/guest ratios revealed that 2-anthracenecarboxylic acid (AC) forms not only 1:1 but also novel 2:1 hydrogen-bonded/π-stacked complexes with a chiral 4-benzamidoprolinol template (TKS159). The 2:1 complexation is a minor process but causes significant CD spectral changes as a consequence of the exciton coupling interaction of two AC chromophores and greatly accelerates the head-to-head photocyclodimerization to significantly affect the stereochemical outcomes.
authors.affiliation: Department of Applied Chemistry, Osaka University, 2-1 Yamadaoka, Suita 565-0871, Japan.
authors.forename: Yuko
authors.initials: Y
authors.lastname: Kawanami
authors.forename: Shin-ya
authors.initials: SY
authors.lastname: Katsumata
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Mizoguchi
authors.forename: Masaki
authors.initials: M
authors.lastname: Nishijima
authors.forename: Gaku
authors.initials: G
authors.lastname: Fukuhara
authors.forename: Cheng
authors.initials: C
authors.lastname: Yang
authors.forename: Tadashi
authors.initials: T
authors.lastname: Mori
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Inoue
mesh_terms: D000873:Anthracenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002942:Circular Dichroism; D019281:Dimerization; D006860:Hydrogen Bonding; D015394:Molecular Structure; D055668:Photochemical Processes; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000873:Anthracenes; D002264:Carboxylic Acids; D011759:Pyrrolidines; C098494:TKS 159; C107996:anthracene-1-carboxylic acid