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Porphyrin-Geländer-Helical Conjugated Banister Type Porphyrin Dyads
Joël F Keller1, Adriano D'Addio1, Marcel Mayor1,2,3
1Department of Chemistry, University of Basel, Basel, Switzerland.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 6, 2026
Summary
A novel Porphyrin-Geländer (PoGe) macrocycle was synthesized, exhibiting tunable optical properties through metal ion exchange. Its enantiomers were successfully resolved and characterized, confirming its potential in advanced materials.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Spectroscopy
Background:
- Porphyrin-based macrocycles are crucial in supramolecular chemistry.
- Geländer molecules offer unique structural scaffolds.
- Tuning photophysical properties is key for advanced applications.
Purpose of the Study:
- To design and synthesize a new Porphyrin-Geländer (PoGe) macrocycle.
- To investigate the effect of central metal ion exchange on spectral properties.
- To resolve and characterize the enantiomers of the synthesized macrocycles.
Main Methods:
- Synthesis of the PoGe macrocycle using a known design principle.
- 2D NMR spectroscopy for structural and symmetry analysis.
- Postsynthesis metal ion exchange (Zn, 2H, Cu).
- Chiral High-Performance Liquid Chromatography (CSP-HPLC) for enantiomeric separation.
- UV-Vis, fluorescence, and Electronic Circular Dichroism (ECD) spectroscopy for characterization.
- Exciton Chirality Method (ECM) for absolute configuration assignment.
Main Results:
- Successful synthesis of the C2-symmetric rac-PoGe[Zn, Zn] macrocycle.
- Postsynthesis modification yielded tunable absorption and emission spectra, extending into the near-IR region.
- Enantiomeric resolution of all synthesized rac-PoGe[M, M] macrocycles.
- Absolute configuration assignment confirmed by ECM and ECD spectral comparison.
Conclusions:
- The Porphyrin-Geländer (PoGe) macrocycle is a versatile platform for tunable photophysical properties.
- Metal ion exchange provides a method for fine-tuning spectral characteristics.
- The developed methods allow for enantiomeric resolution and absolute configuration determination of these complex macrocycles.
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