ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
Pyrrolo[3,2-b]pyrroles-From Unprecedented Solvatofluorochromism to Two-Photon Absorption.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 110 citations in OpenAlex.
- Multiphoton Absorption in Branched Quadrupolar Diquinoxalines for Two-Photon Polymerization Design.ACS physical chemistry Au · 2026Article
- Article
- Computer-Generated, Mechanistic Networks Assist in Assigning the Outcomes of Complex Multicomponent Reactions.Journal of the American Chemical Society · 2025Article
- Shedding new light on quadrupolar 1,4-dihydropyrrolo[3,2-Chemical science · 2025Article
- Strongly Polarized π-Extended 1,4-Dihydropyrrolo[3,2-The Journal of organic chemistry · 2024Article
- Quadrupolar, Highly Polarized Dyes: Emission Dependence on Viscosity and Selective Mitochondria Staining.ACS organic & inorganic Au · 2024Article
- 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
- Chromophore Planarity, -BH Bridge Effect, and Two-Photon Activity: Bi- and Ter-Phenyl Derivatives as a Case Study.The journal of physical chemistry. A · 2023Article
- Entropy-Induced Selectivity Switch in Gold Catalysis: Fast Access to Indolo[1,2-a]quinolines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Targeting of the Mitochondrial TET1 Protein by Pyrrolo[3,2-International journal of molecular sciences · 2022Article
- Review
- Going beyond the borders: pyrrolo[3,2-Chemical science · 2021Article
- Potent strategy towards strongly emissive nitroaromatics through a weakly electron-deficient core.Chemical science · 2021Article
- Deciphering the unusual fluorescence in weakly coupled bis-nitro-pyrrolo[3,2-b]pyrroles.Communications chemistry · 2020Article
- Method for the Large-Scale Synthesis of Multifunctional 1,4-Dihydro-pyrrolo[3,2-The Journal of organic chemistry · 2020Article
- Direct local solvent probing by transient infrared spectroscopy reveals the mechanism of hydrogen-bond induced nonradiative deactivation.Chemical science · 2017Article
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Authors and funding
7 authors at 4 institutions in 4 countries.
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Abstract
A combined experimental and theoretical study of the two-photon absorption (2PA) properties of a series of quadrupolar molecules possessing a highly electron-rich heterocyclic core, pyrrolo[3,2-b]pyrrole, is presented. In agreement with quantum-chemical calculations, large 2PA cross-section values, σ2PA ≈10(2) -10(3) GM (1 GM=10(50) cm(4) s photon(-1) ), are observed at wavelengths of 650-700 nm, which correspond to the two-photon allowed but one-photon forbidden transitions. The calculations also predict that increased planarity of this molecule through removal of two N-substituents leads to further increase in the σ2PA values. Surprisingly, the most quadrupolar pyrrolo[3,2-b]pyrrole derivative, containing two 4-nitrophenyl substituents at positions 2 and 5, demonstrates a very strong solvatofluorochromic effect, with a fluorescence quantum yield as high as 0.96 in cyclohexane, whereas the fluorescence vanishes in DMSO.
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