Sterically Protected and Conformation-Restricted BOBHY Dyes with Bright Near-Infrared Fluorescence: N<sub>2</sub>O-type Expanded BOPHY Dyes Derived from Boronic Acids
Jun Wang, Xingbao Fang, Xing Guo, Qinghua Wu, Qingbao Gong, Changjiang Yu, Erhong Hao, Lijuan Jiao
Abstract
O-type hydrazine-containing bipyrrole boron complexes has been developed via a one-pot condensation of formylisoindole, hydrazine, and various organoboronic acids. Because of the conformation-restricted coplanar structure and the axial-substituted aryl groups, these novel dyes show deep-red absorption, bright near-infrared (NIR) fluorescence in both solution and solid states, and good solubility in organic solvents. The derivative with pyridinium ions also has been synthesized as an NIR mitochondrially targetable fluorescent probe.
Topics & Concepts
ChemistryFluorescenceSteric effectsPyridiniumPhotochemistryHydrazine (antidepressant)SolubilityArylAbsorption (acoustics)BoronCondensationBoron trifluorideOrganic chemistryAlkylThermodynamicsPhysicsAcousticsCatalysisChromatographyQuantum mechanicsLuminescence and Fluorescent MaterialsMolecular Sensors and Ion DetectionSupramolecular Self-Assembly in Materials