title: Toward unidirectional switches: 2-(2-Hydroxyphenyl)pyridine and 2-(2-methoxyphenyl)pyridine derivatives as pH-triggered pivots.
abstract: The pH-induced switching process of 2-(2-hydroxyphenyl)pyridine and 2-(2-methoxyphenyl)pyridine derivatives was investigated with the help of UV spectroscopy. Quantum chemical calculations at the B3LYP/6-31G* level of theory were performed to show that in the case of 2-(2-methoxyphenyl)-3-methylpyridine and 2-(2-hydroxyphenyl)-3-methylpyridine the rotation during the switching process proceeds unidirectionally at the molecular level. If a 2-(2-methoxyphenyl)pyridine derivative is fixed to a chiral cyclopeptidic scaffold, a unidirectional progress of the rotation is achieved macroscopically.
authors.affiliation: Institut für Organische Chemie, Fakultät für Chemie, Universität Duisburg-Essen, Universitätsstraße 7, D-45117 Essen, Germany.
authors.forename: Christina
authors.initials: C
authors.lastname: Tepper
authors.forename: Gebhard
authors.initials: G
authors.lastname: Haberhauer