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Antiaromatic Nanographenes via a BODIPY-Fusion Strategy.

Kaisheng Wang¹, Koshiro Isono¹, Hideaki Takano^1,2

¹Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Integrated Research Consortium on Chemical Sciences (IRCCS), and Research Institute for Quantum and Chemical Innovation, Institutes of Innovation for Future Society, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8603, Japan.

Journal of the American Chemical Society

|November 26, 2025

Summary

Researchers synthesized novel boron dipyrromethene (BODIPY)-fused nanographenes with antiaromatic properties and intense near-infrared (NIR) absorption. These materials show potential for photothermal applications due to their unique electronic and optical characteristics.

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Area of Science:

Organic Chemistry
Materials Science
Nanotechnology

Background:

Synthesizing antiaromatic molecules with near-infrared (NIR) absorption is difficult due to forbidden HOMO-LUMO transitions.
Boron dipyrromethene (BODIPY) dyes are known for their photophysical properties.

Purpose of the Study:

To develop novel antiaromatic molecules with intense NIR absorption.
To explore the synthesis and properties of BODIPY-fused nanographenes.

Main Methods:

Oxidative cyclodehydrogenation to synthesize anthracene- and anthanthrene-fused BODIPY nanographenes.
¹H NMR spectroscopy and theoretical calculations to confirm antiaromaticity.
Electrochemical measurements to determine HOMO-LUMO energy gaps.
Transient-absorption spectroscopy to study excited-state dynamics.
Encapsulation in amphiphilic polymers to create water-soluble nanoparticles.

Main Results:

Successfully synthesized BODIPY-fused nanographenes with distinct antiaromatic characteristics.
Achieved narrow HOMO-LUMO energy gaps as low as 0.84 eV.
Observed NIR absorption up to 1600 nm.
Demonstrated rapid excited-state decay.
Developed water-soluble nanoparticles with high photostability and photothermal conversion efficiencies (68% and 57%).

Conclusions:

The BODIPY-fusion strategy effectively introduces antiaromaticity and NIR absorption into nanographenes.
These novel materials hold promise for advanced applications, including photothermal therapy.