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π-Expanded Dipyrrolonaphthyridinediones with Large Two-Photon Absorption Cross-Section Values.
Bartłomiej Sadowski1, Hanayo Kita2,3, Marek Grzybowski1
1Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
The Journal of Organic Chemistry
|June 29, 2017
Summary
Novel dipyrrolonaphthyridinedione dyes were synthesized for enhanced far-red/NIR absorption and strong two-photon absorption (TPA) capabilities. These compounds exhibit excellent TPA cross-sections and brightness, making them promising for advanced optical applications.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Development of novel organic dyes for optical applications is crucial.
- Far-red/near-infrared (NIR) absorbing dyes with high two-photon absorption (TPA) cross-sections are of significant interest.
Purpose of the Study:
- To develop a synthetic route to novel dipyrrolonaphthyridinedione-based dyes.
- To investigate the photophysical properties, particularly TPA characteristics, of these new dye families.
Main Methods:
- Utilized the Heck reaction for the synthesis of dyes featuring double and triple bond linkages.
- Characterized absorption, fluorescence, and two-photon absorption properties.
- Employed theoretical calculations to understand structure-property relationships.
Main Results:
- Synthesized novel dipyrrolonaphthyridinedione dyes with strong far-red/NIR absorption.
- Achieved high two-photon absorption (TPA) cross-sections (up to 5180 GM for double bonds, 2840 GM for triple bonds) and brightness (up to 1450 GM).
- Demonstrated a beneficial ratio of TPA cross-section to molecular weight (σ2/MW) ranging from 1.6-9.8 GM/g.
Conclusions:
- The developed synthetic strategy provides access to novel TPA materials.
- Peripheral substitution significantly influences TPA enhancement through electron-donating or withdrawing effects.
- These dyes are promising candidates for applications requiring efficient TPA in the far-red/NIR region.
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