Spin Frustration in Molecular Nanocarbons
PI: Marcin Stępień
Grant detailsResearch
Funding
Active and completed research projects supporting the lab.
Active grants
From open-shell materials to molecular recognition: synthesis of polycyclic aromatic compounds through cyclotrimerization of arynes and hetarynes
PI: Arseni Borissov
Grant detailsFrom dendrimers to macrocycles: exploring covalent templates in the synthesis of large aromatic structures
Grant detailsElectron-Deficient Cyclophanes and Annulenes. Functional Aromatics in Two and Three Dimensions
PI: Marcin Stępień
Related publications
- Heptannulated Perylene Diimides: Formation and Reactivity of Electron-Deficient Tropylium Cations and Heptafulvenes. Angew. Chem. Int. Ed. 2025, 64 (7), e202419899. 10.1002/anie.202419899 OA
- Pentacosacyclenes: cruciform molecular nanocarbons based on cyclooctatetraene. Chem. Sci. 2024, 15 (44), 18640–18649. 10.1039/D4SC05938G OA
- Redox–protonation landscape of indene-annulated perylenes: chemodivergent switching of multistate NIR chromophores. Chem. Sci. 2026, Advance Article. 10.1039/D6SC01695B OA
Completed grants
Open-Shell Nanocarbons: Organic Materials and Synthetic Tools
PI: Marcin Stępień
Related publications
- An Open-Shell Coronoid with Hybrid Chichibabin–Schlenk Conjugation. Angew. Chem. Int. Ed. 2021, 60 (41), 22496–22504. 10.1002/anie.202109273 OA
- Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds. Chem. Rev. 2022, 122 (1), 565–788. 10.1021/...ev.1c00449 OA
- Tetrafluorenofulvalene as a sterically frustrated open-shell alkene. Nat. Chem. 2023, 15 (11), 1541–1548. 10.1038/...23-01341-8 OA
- Dinor[7]helicene and Beyond: Divergent Synthesis of Chiral Diradicaloids with Variable Open-Shell Character. Angew. Chem. Int. Ed. 2023, 62 (38), e202309238. 10.1002/anie.202309238 OA
- Triindenotriphenylenes: Spin-Frustrated Triskelion Triradicals with Excellent Ambient Stability. Angew. Chem. Int. Ed. 2024, 63 (36), e202408510. 10.1002/anie.202408510 OA
- Difluorenoheteroles: topological control of π conjugation in diradicaloids and mixed-valence radical ions. Chem. Sci. 2024, 15 (26), 10101–10109. 10.1039/D4SC02459A OA
- Viologen–cycloparaphenylene hybrids: luminescent molecular nanocarbons for anion binding and specific vapor sorption. Org. Chem. Front. 2025, 12 (2), 437–447. 10.1039/D4QO01993H OA
- Heptannulated Perylene Diimides: Formation and Reactivity of Electron-Deficient Tropylium Cations and Heptafulvenes. Angew. Chem. Int. Ed. 2025, 64 (7), e202419899. 10.1002/anie.202419899 OA
Electric Field-Responsive Framework Materials from Aromatic Building Blocks
PI: Marcin Stępień,
Co-PI: Dirk Volkmer (University of Augsburg)
Related publications
- Acenaphtho[1,2-d][1,2,3]triazole and Its Kuratowski Complex: A π-Extended Tecton for Supramolecular and Coordinative Self-Assembly. Chem. Eur. J. 2022, 28 (4), e202103480. 10.1002/chem.202103480 OA
- Tridecacyclene Tetraimide: An Easily Reduced Cyclooctatetraene Derivative. Angew. Chem. Int. Ed. 2022, 61 (38), e202207486. 10.1002/anie.202207486 OA
- Pentacosacyclenes: cruciform molecular nanocarbons based on cyclooctatetraene. Chem. Sci. 2024, 15 (44), 18640–18649. 10.1039/D4SC05938G OA
Curves and Cavities: the Fold-in Method as a Versatile Tool for Synthesizing Complex Aromatics
PI: Marcin Stępień
Related publications
- Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds. Chem. Rev. 2022, 122 (1), 565–788. 10.1021/...ev.1c00449 OA
- Emerging applications of curved aromatic compounds. Trends Chem. 2022, 4 (7), 573–576. 10.1016/...022.04.005 OA
- Feeding a Molecular Squid: A Pliable Nanocarbon Receptor for Electron-Poor Aromatics. J. Am. Chem. Soc. 2020, 142 (36), 15604–15613. 10.1021/jacs.0c07956 OA
- An Open-Shell Coronoid with Hybrid Chichibabin–Schlenk Conjugation. Angew. Chem. Int. Ed. 2021, 60 (41), 22496–22504. 10.1002/anie.202109273 OA
Double C–H Bond Activation: A New Tool for the Synthesis of Extensively Conjugated Oligopyrrole Materials
PI: Liliia Moshniaha · Advisor: Marcin Stępień
Related publications
- Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties. Beilstein J. Org. Chem. 2020, 16 (1), 895–903. 10.3762/bjoc.16.81 OA
- Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds. Chem. Rev. 2022, 122 (1), 565–788. 10.1021/...ev.1c00449 OA
Heterocyclic Nanotube End-caps: Shape, Strain, and Function
PI: Marcin Stępień
Related publications
- Lemniscular [16]Cycloparaphenylene: A Radially Conjugated Figure-Eight Aromatic Molecule. J. Am. Chem. Soc. 2019, 141 (18), 7421–7427. 10.1021/jacs.9b01797 OA
- Electrophilic Aromatic Coupling of Hexapyrrolylbenzenes. A Mechanistic Analysis. J. Org. Chem. 2020, 85 (1), 187–194. 10.1021/acs.joc.9b02556 OA
- Electrochemical Polymerization of Pyrrole–Perimidine Hybrids: Low-Band-Gap Materials with High n-Doping Activity. J. Phys. Chem. C 2020, 124 (26), 14350–14362. 10.1021/acs.jpcc.0c03002 OA
- Feeding a Molecular Squid: A Pliable Nanocarbon Receptor for Electron-Poor Aromatics. J. Am. Chem. Soc. 2020, 142 (36), 15604–15613. 10.1021/jacs.0c07956 OA
- Stereocontrolled Synthesis of Chiral Heteroaromatic Propellers with Small Optical Bandgaps. Angew. Chem. Int. Ed. 2019, 58 (15), 4929–4933. 10.1002/anie.201900175 OA
- Bowls, Hoops, and Saddles: Synthetic Approaches to Curved Aromatic Molecules. Angew. Chem. Int. Ed. 2019, 58 (1), 86–116. 10.1002/anie.201807004
Coronoid hydrocarbons: exploring the fold-in strategy in the synthesis of macrocyclic nanographenes
PI: Marcin A. Majewski · Advisor: Marcin Stępień
Related publications
- Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle. J. Am. Chem. Soc. 2018, 140 (43), 14474–14480. 10.1021/jacs.8b09385 OA
- Octulene: A Hyperbolic Molecular Belt that Binds Chloride Anions. Angew. Chem. Int. Ed. 2016, 55 (45), 14072–14076. 10.1002/anie.201608384
- 5,10-Dimesityldiindeno[1,2-a:2′,1′-i]phenanthrene: a stable biradicaloid derived from Chichibabin's hydrocarbon. Chem. Sci. 2019, 10 (11), 3413–3420. 10.1039/C9SC00170K OA
- Bowls, Hoops, and Saddles: Synthetic Approaches to Curved Aromatic Molecules. Angew. Chem. Int. Ed. 2019, 58 (1), 86–116. 10.1002/anie.201807004
Oligomeric azagraphenoids. Synthesis and properties
PI: Marika Żyła-Karwowska · Advisor: Marcin Stępień
Related publications
- An Electron-Deficient Azacoronene Obtained by Radial π Extension. Angew. Chem. Int. Ed. 2016, 55 (47), 14658–14662. 10.1002/anie.201608400
Extensively Fused Pyrrole-Based Aromatics. Synthetic Methods and Functional Materials
PI: Marcin Stępień
Related publications
- Mechanism of 3,4-diarylpyrrole electrooxidation. Electrochim. Acta 2016, 200, 296–304. 10.1016/...016.03.066
- Bandgap Engineering in π-Extended Pyrroles. A Modular Approach to Electron-Deficient Chromophores with Multi-Redox Activity. J. Am. Chem. Soc. 2016, 138 (35), 11390–11398. 10.1021/jacs.6b07826
- Carbocyclization approaches to electron-deficient nanographenes and their analogues. Org. Chem. Front. 2018, 5 (15), 2395–2414. 10.1039/C8QO00423D
- Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications. Chem. Rev. 2017, 117 (4), 3479–3716. 10.1021/...ev.6b00076
- Pd-Induced Double C–H Bond Activation in Annulative Syntheses of Bipyrrole Boomerangs: Mechanistic Insights from NMR Spectroscopy and Computation. J. Org. Chem. 2018, 83 (9), 5199–5209. 10.1021/acs.joc.8b00630
- An Electron-Deficient Azacoronene Obtained by Radial π Extension. Angew. Chem. Int. Ed. 2016, 55 (47), 14658–14662. 10.1002/anie.201608400
- Electron-Deficient Bipyrrole Boomerangs: Bright Fluorophores Obtained via Double C-H Bond Activation. Chem. Eur. J. 2018, 24 (29), 7525–7530. 10.1002/chem.201801199
Expanded Azacoronenes. Exploring Synthetic Limits in a Congested Molecular Environment
PI: Elżbieta Zielińska · Advisor: Marcin Stępień
Related publications
- Aromatic Nanosandwich Obtained by σ-Dimerization of a Nanographenoid π-Radical. J. Am. Chem. Soc. 2020, 142 (7), 3626–3635. 10.1021/jacs.9b13942 OA
- Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications. Chem. Rev. 2017, 117 (4), 3479–3716. 10.1021/...ev.6b00076
Chrysaoroles. Synthesis and properties
PI: Damian Myśliwiec · Advisor: Marcin Stępień
Related publications
- Stereoselective Wittig Olefination as a Macrocyclization Tool. Synthesis of Large Carbazolophanes. J. Org. Chem. 2015, 80 (12), 6300–6312. 10.1021/acs.joc.5b00745
π-Aromatics on Hyperbolic Planes. Synthesis and Self-Assembly
PI: Marcin Stępień
Related publications
- Fully Conjugated [4]Chrysaorene. Redox-Coupled Anion Binding in a Tetraradicaloid Macrocycle. J. Am. Chem. Soc. 2018, 140 (43), 14474–14480. 10.1021/jacs.8b09385 OA
- Synthesis of a peripherally conjugated 5-6-7 nanographene. Chem. Sci. 2016, 7 (1), 286–294. 10.1039/C5SC03280F OA
- Bowls, Hoops, and Saddles: Synthetic Approaches to Curved Aromatic Molecules. Angew. Chem. Int. Ed. 2019, 58 (1), 86–116. 10.1002/anie.201807004
- Stereoselective Wittig Olefination as a Macrocyclization Tool. Synthesis of Large Carbazolophanes. J. Org. Chem. 2015, 80 (12), 6300–6312. 10.1021/acs.joc.5b00745
- Carbocyclization approaches to electron-deficient nanographenes and their analogues. Org. Chem. Front. 2018, 5 (15), 2395–2414. 10.1039/C8QO00423D
- An Aromatic Riddle: Decoupling Annulene Conjugation in Coronoid Macrocycles. Chem 2018, 4 (7), 1481–1483. 10.1016/...018.06.008
- Chrysaorenes: assembling coronoid hydrocarbons via the fold-in synthesis. Chem. Commun. 2015, 51 (82), 15094–15097. 10.1039/C5CC06046J
- Octulene: A Hyperbolic Molecular Belt that Binds Chloride Anions. Angew. Chem. Int. Ed. 2016, 55 (45), 14072–14076. 10.1002/anie.201608384
- 5,10-Dimesityldiindeno[1,2-a:2′,1′-i]phenanthrene: a stable biradicaloid derived from Chichibabin's hydrocarbon. Chem. Sci. 2019, 10 (11), 3413–3420. 10.1039/C9SC00170K OA
- Highly Strained Nonclassical Nanotube End-caps. A Single-Step Solution Synthesis from Strain-Free, Non-Macrocyclic Precursors. J. Am. Chem. Soc. 2015, 137 (4), 1643–1649. 10.1021/ja511951x
- Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications. Chem. Rev. 2017, 117 (4), 3479–3716. 10.1021/...ev.6b00076
- Heteroaromatic Belts through Fold-in Synthesis: Mechanistic Insights into a Macrocycle-Templated Friedel–Crafts Alkylation. Chem. Eur. J. 2014, 20 (46), 14981–14985. 10.1002/chem.201404470
- Expanded Hexapyrrolohexaazacoronenes. Near-Infrared Absorbing Chromophores with Interrupted Peripheral Conjugation. J. Am. Chem. Soc. 2014, 136 (46), 16399–16410. 10.1021/ja508963v
- An Electron-Deficient Azacoronene Obtained by Radial π Extension. Angew. Chem. Int. Ed. 2016, 55 (47), 14658–14662. 10.1002/anie.201608400
Donor–Acceptor Oligopyrroles for Energy and Electron Transfer. From Aromatic Nanohoops to Photodynamic Therapy
PI: Marcin Stępień
Related publications
- Stereocontrolled Synthesis of Chiral Heteroaromatic Propellers with Small Optical Bandgaps. Angew. Chem. Int. Ed. 2019, 58 (15), 4929–4933. 10.1002/anie.201900175 OA
- Electrophilic Aromatic Coupling of Hexapyrrolylbenzenes. A Mechanistic Analysis. J. Org. Chem. 2020, 85 (1), 187–194. 10.1021/acs.joc.9b02556 OA
- π-Extended Donor–Acceptor Porphyrins and Metalloporphyrins for Antimicrobial Photodynamic Inactivation. Chem. Eur. J. 2020, 26 (37), 8262–8266. 10.1002/chem.201905372 OA
- Aromatic Nanosandwich Obtained by σ-Dimerization of a Nanographenoid π-Radical. J. Am. Chem. Soc. 2020, 142 (7), 3626–3635. 10.1021/jacs.9b13942 OA
- Electrochemical Polymerization of Pyrrole–Perimidine Hybrids: Low-Band-Gap Materials with High n-Doping Activity. J. Phys. Chem. C 2020, 124 (26), 14350–14362. 10.1021/acs.jpcc.0c03002 OA
- Porphyrin-Ryleneimide Hybrids: Low-Bandgap Acceptors in Energy-Transfer Cassettes. Chem. Asian J. 2020, 15 (18), 2854–2858. 10.1002/asia.202000762
- Porphyrin–Ryleneimide Hybrids: Tuning of Visible and Near-Infrared Absorption by Chromophore Desymmetrization. Org. Lett. 2020, 22 (18), 7202–7207. 10.1021/...tt.0c02544 OA
- Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties. Beilstein J. Org. Chem. 2020, 16 (1), 895–903. 10.3762/bjoc.16.81 OA
- Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds. Chem. Rev. 2022, 122 (1), 565–788. 10.1021/...ev.1c00449 OA
- Acenaphtho[1,2-d][1,2,3]triazole and Its Kuratowski Complex: A π-Extended Tecton for Supramolecular and Coordinative Self-Assembly. Chem. Eur. J. 2022, 28 (4), e202103480. 10.1002/chem.202103480 OA
- Naphthalimide-Fused Dipyrrins: Tunable Halochromic Switches and Photothermal NIR-II Dyes. Adv. Sci. 2022, 9 (19), 2105886. 10.1002/advs.202105886 OA
- Helicity Modulation in NIR-Absorbing Porphyrin-Ryleneimides. Angew. Chem. Int. Ed. 2022, 61 (18), e202200781. 10.1002/anie.202200781 OA
- Synthesis of a donor–acceptor heterodimer via trifunctional completive self-sorting. Nat. Commun. 2022, 13 (1), 3204. 10.1038/...22-30859-7 OA
- Acenaphthylene-fused ullazines: fluorescent π-extended monopyrroles with tunable electronic gaps. Org. Chem. Front. 2022, 9 (12), 3179–3185. 10.1039/D2QO00421F
Design and Synthesis of New Porphyrin-Based Materials
PI: Marcin Stępień
Tubular π-Aromatic Compounds: Synthesis and Properties
PI: Marcin Stępień
Related publications
- The Fold-In Approach to Bowl-Shaped Aromatic Compounds: Synthesis of Chrysaoroles. Angew. Chem. Int. Ed. 2013, 52 (6), 1713–1717. 10.1002/anie.201208547
- Synthesis of Bis(phenanthropyrroles) via a Tandem Scholl Oxidation. J. Org. Chem. 2013, 78 (3), 1260–1265. 10.1021/jo302486x
- Recent Advances in the Synthesis of Bowl-Shaped Aromatic Compounds. Synlett 2013, 24 (11), 1316–1321. 10.1055/s-0033-1338456
- Anomalous Stereoselectivity in the Wittig Reaction: The Role of Steric Interactions. J. Org. Chem. 2013, 78 (18), 9512–9516. 10.1021/jo401654f