ArticleThe Journal of organic chemistry2014
Synthesis of phosphorescent asymmetrically π-extended porphyrins for two-photon applications.
Article in The Journal of organic chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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19 citing papers in PubMed, 54 citations in OpenAlex.
- Synthesis and Intramolecular Charge Transfer Studies onMolecules (Basel, Switzerland) · 2026Article
- Synthesis and Optical Properties of Unsymmetric Aromatically π-Extended BODIPY.The Journal of organic chemistry · 2025Article
- Assessment of Conjugation Pathways inThe Journal of organic chemistry · 2024Article
- Unsymmetric Pentacene- and Pentacenequinone-Fused Porphyrins: Understanding the Effect of Cross- and Linear-Conjugation.ACS physical chemistry Au · 2022Article
- Optical measurement of microvascular oxygenation and blood flow responses in awake mouse cortex during functional activation.Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism · 2022Article
- Recent Progress in Near-Infrared Organic Electroluminescent Materials.Topics in current chemistry (Cham) · 2021Review
- Article
- Three-Photon Spectroscopy of Porphyrins.The journal of physical chemistry. A · 2020Article
- Cerebrovascular Blood Flow Design and Regulation; Vulnerability in Aging Brain.Frontiers in physiology · 2020Review
- Current Advances in the Synthesis of Valuable Dipyrromethane Scaffolds: Classic and New Methods.Molecules (Basel, Switzerland) · 2019Review
- X-ray Structure Elucidation of a Pt-Metalloporphyrin and Its Application for Obtaining Sensitive AuNPs-Plasmonic Hybrids Capable of Detecting Triiodide Anions.International journal of molecular sciences · 2019Article
- New red-emitting Schiff base chelates: promising dyes for sensing and imaging of temperature and oxygenJournal of materials chemistry. C · 2018Article
- Review
- Two-Photon Absorbing Phosphorescent Metalloporphyrins: Effects of π-Extension and Peripheral Substitution.Journal of the American Chemical Society · 2016Article
- Two-photon microscopy measurement of cerebral metabolic rate of oxygen using periarteriolar oxygen concentration gradients.Neurophotonics · 2016Article
- Modeling of Cerebral Oxygen Transport Based on In vivo Microscopic Imaging of Microvascular Network Structure, Blood Flow, and Oxygenation.Frontiers in computational neuroscience · 2016Review
- Bright, "Clickable" Porphyrins for the Visualization of Oxygenation under Ambient Light.Angewandte Chemie (International ed. in English) · 2015Article
- Long-wavelength analyte-sensitive luminescent probes and optical (bio)sensors.Methods and applications in fluorescence · 2015Article
- High-resolution in vivo optical imaging of stroke injury and repair.Brain research · 2015Review
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2 authors at 1 institution in 1 country.
Funding
Abstract
Significant effort has been directed in recent years toward porphyrins with enhanced two-photon absorption (2PA). However, the properties of their triplet states, which are central to many applications, have rarely been examined in parallel. Here we report the synthesis of asymmetrically π-extended platinum(II) and palladium(II) porphyrins, whose 2PA into single-photon-absorbing states is enhanced as a result of the broken center-of-inversion symmetry and whose triplet states can be monitored by room-temperature phosphorescence. 5,15-Diaryl-syn-dibenzoporphyrins (DBPs) and syn-dinaphthoporphyrins (DNPs) were synthesized by [2 + 2] condensation of the corresponding dipyrromethanes and subsequent oxidative aromatization. Butoxycarbonyl groups on the meso-aryl rings render these porphyrins well-soluble in a range of organic solvents, while 5,15-meso-aryl substitution causes minimal nonplanar distortion of the macrocycle, ensuring high triplet emissivity. A syn-DBP bearing four alkoxycarbonyl groups in the benzo rings and possessing a large static dipole moment was also synthesized. Photophysical properties (2PA brightness and phosphorescence quantum yields and lifetimes) of the new porphyrins were measured, and their ground-state structures were determined by DFT calculations and/or X-ray analysis. The developed synthetic methods should facilitate the construction of π-extended porphyrins for applications requiring high two-photon triplet action cross sections.
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