The DOI matches its Crossref record.
5,10,15,20‐Tetraphenylsapphyrin‐Identification of a Pentapyrrolic Expanded Porphyrin in the Rothemund Synthesis
Abstract
The Rothemund‐type condensation of pyrrole and benzaldehyde yields, apart from 5,10,15,20‐tetraphenylporphyrin (TPPH 2) and inverted tetraphenylporphyrin 2‐aza‐21‐carba‐5,10,15,20‐tetraphenylporphyrin (CTPPH 2), a unique pentapyrrolic macrocyclic molecule with the aromatic nucleus of sapphyrin, namely, 5,10,15,20‐tetraphenylsapphyrin (TPSH 3). Its unorthodox structural skeleton with an inverted pyrrole ring lying opposite to the bipyrrole unit accounts for the spectroscopic properties of the novel sapphyrin. The diprotonation of TPSH 3 acts as a trigger for a structural transformation involving a flip of the pyrrole units, which relocates the 27‐NH pyrrolic nitrogen from the periphery into the center of the macrocycle. The formation of 5,10,15,20‐tetraphenylsapphyrin proves that the pentapyrrolic product is accessible by the mechanism of the Rothemund synthesis.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cited by
Chemistry of meso-Aryl-Substituted Expanded Porphyrins: Aromaticity and Molecular Twist
Tanaka, T., & Osuka, A. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00371 · Cited by 490
Figure Eights, Möbius Bands, and More: Conformation and Aromaticity of Porphyrinoids
Stępień, M., Sprutta, N., & Latos‐Grażyński, L. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201003353 · Cited by 481
Self-citationmeso-Aryl-Substituted Expanded Porphyrins
Shin, J.-Y., Furuta, H., Yoza, K., Igarashi, S., & Osuka, A. (2001) · Journal of the American Chemical Society · doi:10.1021/ja0106624 · Cited by 349
Metadata
- Authors
- Chmielewski, P. J., Latos‐Grażyński, L., & Rachlewicz, K.
- Venue
- Chemistry – A European Journal
- Publisher
- Wiley
- Published
- 1995-04
- Volume
- 1
- Issue
- 1
- Pages
- 68-73
- ISSN
- 0947-6539 (ISSN-L)
- 1521-3765
- OpenAlex
- W2044076100
- Cited by
- 162
- References
- 0
- FWCI
- 5.29
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
How to cite
Cite CoChat for the checks on this page, and the paper for its own findings.
- This page
- CoChat. (2026). Citation check: 5,10,15,20‐Tetraphenylsapphyrin‐Identification of a Pentapyrrolic Expanded Porphyrin in the Rothemund Synthesis. https://app.cochat.ai/papers/10.1002/chem.19950010111
- The paper
- Chmielewski, P. J., Latos‐Grażyński, L., & Rachlewicz, K. (1995). 5,10,15,20‐Tetraphenylsapphyrin‐Identification of a Pentapyrrolic Expanded Porphyrin in the Rothemund Synthesis. Chemistry – A European Journal. https://doi.org/10.1002/chem.19950010111
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
