Synthesis of β-Pyridyl α-Amino Acids: Conformationally Sensitive Charge Transfer-Based Fluorophores

Autor: Riley, Leanne M., Marshall, Olivia, Harkiss, Alexander H., Senn, Hans M., Sutherland, Andrew
Zdroj: Organic Letters; 20240101, Issue: Preprints
Abstrakt: Unnatural α-amino acids with charge transfer-based poly aromatic side chains have been designed as conformationally sensitive fluorophores. These were prepared using a hetero-Diels–Alder reaction and a Knoevenagel–Stobbe process to generate a biaryl pyridyl unit, followed by iron-catalyzed bromination and a Suzuki–Miyaura cross-coupling reaction to complete the triaryl system. A photophysical study led to the discovery of a p-methoxy analogue which exhibited viscosity-sensitive fluorescence in which emission could be controlled between twisted and planar conformations.
Databáze: Supplemental Index