ArticleChemical science2021
Potent strategy towards strongly emissive nitroaromatics through a weakly electron-deficient core.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 33 citations in OpenAlex.
- One-Pot Synthesis of Dihydrothiazole-Hydrazone Hybrids and Evaluation of Their Absorption and Emission Properties.Journal of fluorescence · 2026Article
- Synthesis and Characterization of Polynorbornenes with Nitronaphthyl Side-Chains.Macromolecular rapid communications · 2025Article
- Shedding new light on quadrupolar 1,4-dihydropyrrolo[3,2-Chemical science · 2025Article
- Dipyrrolonaphthyridinedione - (still) a mysterious cross-conjugated chromophore.Chemical science · 2023Review
- Solvatochromic and Aggregation-Induced Emission Active Nitrophenyl-Substituted Pyrrolidinone-Fused-1,2-Azaborine with a Pre-Twisted Molecular Geometry.Journal of materials chemistry. C · 2023Article
- Article
- Leveraging Coupled Solvatofluorochromism and Fluorescence Quenching in Nitrophenyl-Containing Thiazolothiazoles for Efficient Organic Vapor Sensing.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Review
- Photophysics and Electrochemistry of Biomimetic Pyranoflavyliums: What Can Bioinspiration from Red Wines Offer?Photochem · 2022Article
- Making Nitronaphthalene Fluoresce.The journal of physical chemistry letters · 2021Article
Corrections and comments
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Authors and funding
16 authors at 6 institutions in 2 countries.
Funding
Abstract
Nitroaromatics seldom fluoresce. The importance of electron-deficient (n-type) conjugates, however, has inspired a number of strategies for suppressing the emission-quenching effects of the strongly electron-withdrawing nitro group. Here, we demonstrate how such strategies yield fluorescent nitroaryl derivatives of dipyrrolonaphthyridinedione (DPND). Nitro groups near the DPND core quench its fluorescence. Conversely, nitro groups placed farther from the core allow some of the highest fluorescence quantum yields ever recorded for nitroaromatics. This strategy of preventing the known processes that compete with photoemission, however, leads to the emergence of unprecedented alternative mechanisms for fluorescence quenching, involving transitions to dark nπ* singlet states and aborted photochemistry. Forming nπ* triplet states from ππ* singlets is a classical pathway for fluorescence quenching. In nitro-DPNDs, however, these ππ* and nπ* excited states are both singlets, and they are common for nitroaryl conjugates. Understanding the excited-state dynamics of such nitroaromatics is crucial for designing strongly fluorescent electron-deficient conjugates.
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Registered trials
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