ArticleThe journal of physical chemistry. A2008
Effects of structural deformations on optical properties of tetrabenzoporphyrins: free-bases and Pd complexes.
Article in The journal of physical chemistry. A, 2008. 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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22 citing papers in PubMed, 113 citations in OpenAlex.
- Size-dependent modulation of intersystem crossing and singlet oxygen sensitization in porphyrin-silver cluster hybrid systems.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2026Article
- Development of bright NIR-emitting pressure-sensitive paints using benzoporphyrin luminophores.Chemical science · 2025Article
- Chirogenesis in Zinc Porphyrins: Theoretical Evaluation of Electronic Transitions, Controlling Structural Factors and Axial Ligation.Chemphyschem : a European journal of chemical physics and physical chemistry · 2021Article
- Article
- Three-Photon Spectroscopy of Porphyrins.The journal of physical chemistry. A · 2020Article
- A Comprehensive Study on Tetraaryltetrabenzoporphyrins.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Oxyphor 2P: A High-Performance Probe for Deep-Tissue Longitudinal Oxygen Imaging.Cell metabolism · 2019Article
- Luminescent ruffled iridium(iii) porphyrin complexes containing N-heterocyclic carbene ligands: structures, spectroscopies and potent antitumor activities under dark and light irradiation conditions.Chemical science · 2019Article
- Energetics of Saddling versus Ruffling in Metalloporphyrins: Unusual Ruffled Dodecasubstituted Porphyrins.ACS omega · 2017Article
- Two-Photon Absorbing Phosphorescent Metalloporphyrins: Effects of π-Extension and Peripheral Substitution.Journal of the American Chemical Society · 2016Article
- Tuning the Structure and Photophysics of a Fluorous Phthalocyanine Platform.The journal of physical chemistry. A · 2016Article
- Palladium(0) NHC complexes: a new avenue to highly efficient phosphorescence.Chemical science · 2015Article
- Synthesis of phosphorescent asymmetrically π-extended porphyrins for two-photon applications.The Journal of organic chemistry · 2014Article
- Two-photon antenna-core oxygen probe with enhanced performance.Analytical chemistry · 2014Article
- β-Pyrazino-fused tetrarylporphyrins.Dyes and pigments : an international journal · 2013Article
- Two new "protected" oxyphors for biological oximetry: properties and application in tumor imaging.Analytical chemistry · 2011Article
- Evaluation of phototoxicity of dendritic porphyrin-based phosphorescent oxygen probes: an in vitro study.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2011Article
- Two-photon microscopy of oxygen: polymersomes as probe carrier vehicles.The journal of physical chemistry. B · 2010Article
- Highly non-planar dendritic porphyrin for pH sensing: observation of porphyrin monocation.Inorganic chemistry · 2010Article
- Pi-extended dipyrrins capable of highly fluorogenic complexation with metal ions.Journal of the American Chemical Society · 2010Article
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
Abstract
A recently developed method of synthesis of pi-extended porphyrins made it possible to prepare a series of tetrabenzoporphyrins (TBP) with different numbers of meso-aryl substituents. The photophysical parameters of free-bases and Pd complexes of meso-unsubstituted TBP's, 5,15-diaryl-TBP's (Ar2TBP's) and 5,10,15,20-tetraaryl-TBP's (Ar4TBP's) were measured. For comparison, similarly meso-arylsubstituted porphyrins fused with nonaromatic cyclohexeno-rings, i.e. Ar(n)-tetracyclohexenoporphyrins (Ar(n)TCHP's, n = 0, 2, 4), were also synthesized and studied. Structural information was obtained by ab initio (DFT) calculations and X-ray crystallography. It was found that: 1) Free-base Ar4TBP's are strongly distorted out-of-plane (saddled), possess broadened, red-shifted spectra, short excited-state lifetimes and low fluorescence quantum yields (tau(fl) = 2-3 ns, phi(fl) = 0.02-0.03). These features are characteristic of other nonplanar free-base porphyrins, including Ar4TCHP's. 2) Ar2TBP free-bases possess completely planar geometries, although with significant in-plane deformations. These deformations have practically no effect on the singlet excited-state properties of Ar2TBP's as compared to planar meso-unsubstituted TBP's. Both types of porphyrins retain strong fluorescence (tau(fl) = 10-12 ns, phi(fl) = 0.3-0.4), and their radiative rate constants (k(r)) are 3-4 times higher than those of planar H2TCHP's. 3) Nonplanar deformations dramatically enhance nonradiative decay of triplet states of regular Pd porphyrins. For example, planar PdTCHP phosphoresces with high quantum yield (phi(phos) = 0.45, tau(phos) = 1118 micros), while saddled PdPh4TCHP is practically nonemissive. In contrast, both ruffled and saddled PdAr(n)TBP's retain strong phosphorescence at ambient temperatures (PdPh2TBP: tau(phos) = 496 micros, phi(phos) = 0.15; PdPh4TBP: tau(phos) = 258 micros, phi(phos) = 0.08). It appears that pi-extension is capable of counterbalancing deleterious effects of nonplanar deformations on triplet emissivity of Pd porphyrins.
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