Nitrogen-Doped Dehydrobenzoannulene as an Electron Acceptor Enabling Trace Epinephrine Analysis

Area of Science:

• Organic Chemistry
• Materials Science
• Analytical Chemistry

Background:

• Electron donor-acceptor (D-A) architectures are crucial in optoelectronic materials.
• Dehydrobenzoannulenes offer unique structural properties for molecular design.
• Nitrogen doping can significantly tune electronic and optical properties.

Purpose of the Study:

• To synthesize novel D-A architectures using dehydrobenzoannulene and azadehydrobenzoannulene acceptors.
• To investigate the impact of nitrogen doping on photophysical and electrochemical properties.
• To develop a sensor for epinephrine detection for neurodegenerative disease diagnosis.

Main Methods:

• Divergent synthesis of three D-A architectures.
• Solvent-dependent fluorescence spectroscopy.
• Density functional theory (DFT) calculations.
• Electrochemical measurements.
• Sensor construction and assay development.

Main Results:

• Successful synthesis of D-A molecules with varying electronic properties.
• Azadehydrobenzoannulene derivative exhibited red-shifted fluorescence and enhanced bipolar electrochemiluminescence.
• Intramolecular charge transfer (ICT) properties were confirmed.
• An epinephrine sensor demonstrated sensitive detection capabilities.

Conclusions:

• Nitrogen doping in dehydrobenzoannulene acceptors enhances fluorescence and electrochemiluminescence.
• The synthesized D-A molecules possess tunable ICT properties.
• An azadehydrobenzoannulene-based sensor shows promise for early neurodegenerative disease diagnosis.