Adolf von Baeyer – Nobelpreisträger für Chemie 1905

A two‐step, one‐flask synthesis of central seven‐membered borondifluoride‐3,3‐dimethyl‐2‐[2‐(2‐pyrrolyl)ethenyl] indole (BOPYIN) ligands has been developed by using the unexplored 3,3‐dimethyl‐2‐[2‐(2‐pyrrolyl)ethenyl] indole. The simple synthetic approach has enabled modification of the electronic structure by changing the substituents on the indole unit. X‐ray analysis indicated that conformations of the seven‐membered BF2 complex including BOPYIN and diazaborepin differ from that of the five‐ and six‐membered organoboron complexes. Interestingly, the bond angle of the N⋅⋅⋅B−N bond increases with the number of atoms in the core ring, based on Baeyer strain theory. These unsymmetric BOPYIN derivatives have excellent photophysical properties, including high fluorescence quantum yields, except for BOPYIN‐4 in the solution state, large Stokes shifts, and good molar absorptivity. The dipole moment of BOPYIN‐3 in the first excited singlet state and ground state was demonstrated by a linear Lippert–Mataga plot. The absorption and emission spectra were not mirror images for BOPYIN‐1–3 and 5, in contradiction to Kasha's rule, as determined by TDDFT. The synthesized BOPYINs have been shown to be biocompatible fluorophores in cell bioimaging.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Adolf von Baeyer – Nobelpreisträger für Chemie 1905

Cited by 4 publications

References 32 publications

Selective Reduction of Barbituric Acids Using SmI₂/H₂O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

Selective Reduction of Barbituric Acids Using SmI₂/H₂O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

Selective Reduction of Barbituric Acids Using SmI₂/H₂O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

A Simple Central Seven‐Membered BOPYIN: Synthesis, Structural, Spectroscopic Properties, and Cellular Imaging Application

Contact Info

Product

Resources

About

Adolf von Baeyer – Nobelpreisträger für Chemie 1905

Cited by 4 publications

References 32 publications

Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

A Simple Central Seven‐Membered BOPYIN: Synthesis, Structural, Spectroscopic Properties, and Cellular Imaging Application

Contact Info

Product

Resources

About

Selective Reduction of Barbituric Acids Using SmI₂/H₂O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

Selective Reduction of Barbituric Acids Using SmI₂/H₂O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts

Selective Reduction of Barbituric Acids Using SmI₂/H₂O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts