A novel synthesis of stable 3H-pyrrolizine fused diazaborepin

Li, Yujiao; Yan, Jiaying; Xiao, Shuzhang; Bao, Zhang; Lu, Futai; Cheng, Kai; Li, Dejiang; Feng, Yaqing; Zhang, Nuonuo

doi:10.1016/j.tetlet.2016.06.052

Cited by 19 publications

(2 citation statements)

References 41 publications

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“…By following the modified procedure, a mixture of product 1 (2.0 mmol) and 2‐formylpyrrole 2 (2.0 mmol) in EtOH (48 mL) was stirred under reflux for 1 h. After completion of the reaction, as confirmed by TLC, the crude product was purified by flash chromatography (silica gel) to afford compound 3 with trans and cis isomer ratio ca. 15:1 for different substituents.…”

Section: Methodsmentioning

confidence: 99%

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

Zhang

Yan

et al. 2019

Chemistry A European J

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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.

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Section: Methodsmentioning

confidence: 99%

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

Zhang

Yan

et al. 2019

Chemistry A European J

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“…Very recently, the original dye of stable BOPYIN (DAB) with a twisted saddle shape, high fluorescence quantum yield and large stokes shift (more than 70 nm) has been reported. [5] It is necessary to study its postfunctionalization due to its structural modification on positions of DAB such as oxidation, substitution reaction and intramolecular oxygen-fluorine displacement reactions. Dialkoxyl BODIPYs have been designed to generate a boron-oxygen fluorophore under the condition of Lewis acid AlCl 3 or strong base NaH/NaOMe.…”

Section: Introductionmentioning

confidence: 99%

Pyrrolizinone‐Fused BOPYINs: Characterization and Selective C‐O Bond Formation Mechanism

Liu

Chen

et al. 2021

ChemistrySelect

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Two novel pyrrolizinone-fused BOPYINs (DABÀ M and DABÀ U) were prepared in one-step through the oxidative and/or oxidative nucleophilic substitution of hydrogen (ONSH) reaction. Selective methoxyl substitution of α-unsubstituted BO-PYIN was developed, in which C À O and C=O bonds were formed and demonstrated by the single crystal structure of DABÀ M. The absorption and emission spectra of both com-pounds showed red shift and large Stokes Shift compared with starting material DAB. Based on the TD-DFT calculation, the electron transfer direction is totally different from DAB due to the carbonyl group on pyrrolizinone unit. Besides, a reasonable mechanism has been proposed and evidenced by quantum calculation in which the relative free energy has been exhibited.

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Construction of Boron Difluoride Complexes with Asymmetric N,N’‐Bidentate Ligands

Zhao,

Ren,

Zhou

2024

Chemistry A European J

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Boron difluoride (BF2) complexes with asymmetrical N,N’‐bidentate ligands have received increasing attention due to their fascinating properties and broad applications. They are generally constructed in two steps: ligand formation, followed by boron complexation. This review focuses on categorizing these BF2 complexes based on the key synthetic strategies that have been applied in the ligand formation steps. The post‐functionalization, properties and applications of different types of BF2 complexes are presented. Their challenges and opportunities are also discussed. This should help the future rational design and synthesis of BF2 complexes with intriguing properties and practical applications.

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A novel synthesis of stable 3H-pyrrolizine fused diazaborepin

Cited by 19 publications

References 41 publications

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

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

Pyrrolizinone‐Fused BOPYINs: Characterization and Selective C‐O Bond Formation Mechanism

Construction of Boron Difluoride Complexes with Asymmetric N,N’‐Bidentate Ligands

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