ArticleCommunications chemistry2020
Deciphering the unusual fluorescence in weakly coupled bis-nitro-pyrrolo[3,2-b]pyrroles.
Article in Communications chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed.
- One-Pot Synthesis of Dihydrothiazole-Hydrazone Hybrids and Evaluation of Their Absorption and Emission Properties.Journal of fluorescence · 2026Article
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- Excited-state intramolecular charge transfer dynamics in 4-methoxy-4'-nitrostilbene: excitation wavelength and solvent dependence.RSC advances · 2026Article
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- Fluorescent solvatochromism and nonfluorescence processes of charge-transfer-type molecules with a 4-nitrophenyl moiety.RSC advances · 2025Article
- 1,4-Dihydropyrrolo[3,2-b]Pyrroles Containing New A-D-A System: Synthesis and Investigation of Their Photophysical Properties.Journal of fluorescence · 2025Article
- Twisting, Hydrogen Bonding, Exciplex Formation, and Charge Transfer. What Makes a Bright Fluorophore Not So Bright?The Journal of organic chemistry · 2025Article
- Computer-Generated, Mechanistic Networks Assist in Assigning the Outcomes of Complex Multicomponent Reactions.Journal of the American Chemical Society · 2025Article
- Selective Tuning of Benzothiadiazole Functionality Enables High Crystallinity and Mobility in RegiorandomMacromolecules · 2025Article
- Shedding new light on quadrupolar 1,4-dihydropyrrolo[3,2-Chemical science · 2025Article
- The magic of biaryl linkers: the electronic coupling through them defines the propensity for excited-state symmetry breaking in quadrupolar acceptor-donor-acceptor fluorophores.Chemical science · 2023Article
- Leveraging Coupled Solvatofluorochromism and Fluorescence Quenching in Nitrophenyl-Containing Thiazolothiazoles for Efficient Organic Vapor Sensing.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Optical Window to Polarity of Electrolyte Solutions.Molecules (Basel, Switzerland) · 2023Article
- An expeditious synthesis of 6,7-dihydrodibenzo[RSC advances · 2022Article
- Review
- Iodine-Catalyzed Multicomponent Synthesis of Highly Fluorescent Pyrimidine-Linked Imidazopyridines.ACS omega · 2022Article
- From 2,5-Diformyl-1,4-dihydropyrrolo[3,2-Organic letters · 2022Article
- Photophysics and Electrochemistry of Biomimetic Pyranoflavyliums: What Can Bioinspiration from Red Wines Offer?Photochem · 2022Article
- Potent strategy towards strongly emissive nitroaromatics through a weakly electron-deficient core.Chemical science · 2021Article
- Making Nitronaphthalene Fluoresce.The journal of physical chemistry letters · 2021Article
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Authors and funding
8 authors.
Funding
Abstract
Electron-deficient π-conjugated functional dyes lie at the heart of organic optoelectronics. Adding nitro groups to aromatic compounds usually quenches their fluorescence via inter-system crossing (ISC) or internal conversion (IC). While strong electronic coupling of the nitro groups with the dyes ensures the benefits from these electron-withdrawing substituents, it also leads to fluorescence quenching. Here, we demonstrate how such electronic coupling affects the photophysics of acceptor-donor-acceptor fluorescent dyes, with nitrophenyl acceptors and a pyrrolo[3,2-b]pyrrole donor. The position of the nitro groups and the donor-acceptor distance strongly affect the fluorescence properties of the bis-nitrotetraphenylpyrrolopyrroles. Concurrently, increasing solvent polarity quenches the emission that recovers upon solidifying the media. Intramolecular charge transfer (CT) and molecular dynamics, therefore, govern the fluorescence of these nitro-aromatics. While balanced donor-acceptor coupling ensures fast radiative deactivation and slow ISC essential for large fluorescence quantum yields, vibronic borrowing accounts for medium dependent IC via back CT. These mechanistic paradigms set important design principles for molecular photonics and electronics.
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