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Near-Infrared Quadrupolar Chromophores Combining Three-Coordinate Boron-Based Superdonor and Superacceptor Units
Tom E Stennett1,2, Philipp Bissinger1,2, Stefanie Griesbeck1,2
1Institute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Angewandte Chemie (International Ed. in English)
|February 20, 2019
Summary
Two new diborene-based chromophores exhibit strong near-infrared absorption due to their unique acceptor-π-donor-π-acceptor structure. These molecules show potential for applications requiring efficient light absorption in the near-infrared spectrum.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Development of novel chromophores with tailored electronic properties is crucial for advanced optical applications.
- Acceptor-π-donor-π-acceptor (A-π-D-π-A) molecular architectures are known for their tunable photophysical characteristics.
Purpose of the Study:
- To synthesize and characterize new A-π-D-π-A chromophores incorporating a diborene core.
- To investigate the impact of strong π-donor (diborene) and π-acceptor (diarylboryl) groups on electronic and optical properties.
Main Methods:
- Synthesis of novel diborene-based chromophores.
- Characterization using NMR spectroscopy, X-ray crystallography, cyclic voltammetry, and UV/Vis-NIR absorption/emission spectroscopy.
Main Results:
- Successful preparation of two new A-π-D-π-A chromophores with diborene cores and diarylboryl end groups.
- Extended π-conjugation across the B4C8 core was confirmed.
- Achieved very small HOMO-LUMO gaps, leading to strong near-infrared absorption (maxima at 840 and 1092 nm in THF) with high extinction coefficients (ca. 120,000 M⁻¹cm⁻¹).
- Observed weak near-infrared fluorescence with small Stokes shifts.
Conclusions:
- The combination of potent diborene donors and diarylboryl acceptors results in efficient near-infrared absorption.
- These novel chromophores demonstrate significant potential for applications in near-infrared optoelectronics.
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