2-Hydroxyanthracene (HA) in its neutral form smoothly photocyclodimerized to four stereoisomeric [4 + 4]-cyclodimers, which were isolated and characterized for the first time, whereas the anionic form of HA turned out to be photochemically inert. Enantiodifferentiating photocyclodimerization of HA in the presence of a chiral hydrogen-bonding template (TKS159), γ-cyclodextrin (γ-CDx) and bovine serum albumin (BSA) was examined to afford chiral syn-head-to-tail and anti-head-to-head cyclodimers in modest enantiomeric excesses with TKS159 and γ-CDx, but practically no photocyclodimerization proceeded in the presence of BSA probably due to the ionization of HA in the binding sites.

21 Sep 2012·Organic LettersQ1 · CHEMISTRY

Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylic Acid via Competitive Binary/Ternary Hydrogen-Bonded Complexes with 4-Benzamidoprolinol

Q1 · CHEMISTRY

Article

Author: Fukuhara, Gaku ; Nishijima, Masaki ; Yang, Cheng ; Mizoguchi, Jun-ichi ; Kawanami, Yuko ; Katsumata, Shin-ya ; Inoue, Yoshihisa ; Mori, Tadashi

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.

16 Oct 2009·The Journal of Organic ChemistryQ2 · CHEMISTRY

Supramolecular Complexation and Enantiodifferentiating Photocyclodimerization of 2-Anthracenecarboxylic Acid with 4-Aminoprolinol Derivatives as Chiral Hydrogen-Bonding Templates

Q2 · CHEMISTRY

Article

Author: Bohne, Cornelia ; Mizoguchi, Jun-ichi ; Pace, Tamara C. S. ; Yanagi, Toshiharu ; Nishijima, Masaki ; Kawanami, Yuko ; Mori, Tadashi ; Wada, Takehiko ; Inoue, Yoshihisa

The photochirogenesis of 2-anthracenecarboxylic acid (AC) complexed to a hydrogen-bonding template (TKS159) was investigated to obtain mechanistic information on how chirogenesis is achieved for the dimerization of AC. Complexation of AC to TKS159 leads to the shielding of one of the two surfaces of the prochiral AC molecule. The two diastereomeric AC-TKS complexes, i.e., re-AC-TKS and si-AC-TKS, were characterized by changes in the UV-vis, fluorescence, and circular dichroism spectra and excited-state lifetimes. The ee is not simply determined by the diastereomeric ratio of the re- and si-AC-TKS complexes but also depends on the relative lifetimes of the diastereomeric complexes. The relative population of the re and si complexes was calculated from the enantiomeric excess (ee) for the products, taking into account the relative lifetimes of the two complexes. These studies established a protocol that can be used to reveal the mechanism for photochirogenesis by investigating the ground state and the excited state behavior of supramolecular systems.

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Indication	Highest Phase	Country/Location	Organization	Date
Gastrointestinal motility disorder	Discovery	Japan	Teikoku Chemical Industries Co., Ltd.	-

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