@article{MTMT:35416944, title = {Aza-annulation reactions extend π-conjugated systems}, url = {https://m2.mtmt.hu/api/publication/35416944}, author = {Bogner, Marcell M. and London, Gábor}, doi = {10.1038/s44160-024-00615-4}, journal-iso = {NAT SYNTH}, journal = {NATURE SYNTHESIS}, unique-id = {35416944}, year = {2024}, eissn = {2731-0582}, orcid-numbers = {Bogner, Marcell M./0009-0007-1397-4575; London, Gábor/0000-0001-6078-3180} } @{MTMT:34827442, title = {Light-activated Molecular Switches, Machines and Motors}, url = {https://m2.mtmt.hu/api/publication/34827442}, author = {Kunfi, Attila and London, Gábor}, booktitle = {Reference Module in Chemistry, Molecular Sciences and Chemical Engineering}, doi = {10.1016/B978-0-443-15742-4.00031-4}, unique-id = {34827442}, year = {2024} } @article{MTMT:34821706, title = {Revisiting Hafner’s Azapentalenes: The Chemistry of 1,3-Bis(dimethylamino)-2-azapentalene}, url = {https://m2.mtmt.hu/api/publication/34821706}, author = {Meiszter, Enikő and Gazdag, Tamás and Mayer, Péter József and Kunfi, Attila and Holczbauer, Tamás and Sulyok-Eiler, Máté and London, Gábor}, doi = {10.1021/acs.joc.3c02564}, journal-iso = {J ORG CHEM}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, volume = {89}, unique-id = {34821706}, issn = {0022-3263}, abstract = {Stable azaheterocyclic derivatives of pentalene have been reported by the group of Hafner in the 1970s. However, these structures remained of low interest until recently, when they started to be investigated in the context of organic light-emitting diodes’ (OLEDs’) development. Herein, we revisit the synthesis of stable azapentalene derivative 1,3-bis(dimethylamino)-2-azapentalene and further explore its properties both computationally and experimentally. Beyond the reproduction and optimization of some previously reported transformations, such as formylation and amine substitution, the available scope of reactions was expanded with azo-coupling, selective halogenations, and cross-coupling reactions. © 2024 The Authors. Published by American Chemical Society.}, year = {2024}, eissn = {1520-6904}, pages = {5941-5951}, orcid-numbers = {Mayer, Péter József/0000-0003-4891-3119; Sulyok-Eiler, Máté/0000-0002-3968-8776} } @article{MTMT:34571192, title = {An Exploration of Substituent Effects on the Photophysical Properties of Monobenzopentalenes}, url = {https://m2.mtmt.hu/api/publication/34571192}, author = {Gazdag, Tamás and Meiszter, Enikő and Mayer, Péter József and Holczbauer, Tamás and Ottosson, Henrik and Maurer, Andrew B. and Abrahamsson, Maria and London, Gábor}, doi = {10.1002/cphc.202300737}, journal-iso = {CHEMPHYSCHEM}, journal = {CHEMPHYSCHEM: A EUROPEAN JOURNAL OF CHEMICAL PHYSICS AND PHYSICAL CHEMISTRY}, volume = {25}, unique-id = {34571192}, issn = {1439-4235}, abstract = {Monobenzopentalenes have received moderate attention compared to dibenzopentalenes, yet their accessibility as stable, non‐symmetric structures with diverse substituents could be interesting for materials applications, including molecular photonics. Recently, monobenzopentalene was considered computationally as a potential chromophore for singlet fission (SF) photovoltaics. To advance this compound class towards photonics applications, the excited state energetics must be characterized, computationally and experimentally. In this report we synthesized a series of stable substituted monobenzopentalenes and provided the first experimental exploration of their photophysical properties. Structural and opto‐electronic characterization revealed that all derivatives showed 1H NMR shifts in the olefinic region, bond length alternation in the pentalene unit, low‐intensity absorptions reflecting the ground‐state antiaromatic character and in turn the symmetry forbidden HOMO‐to‐LUMO transitions of ~2 eV and redox amphotericity. This was also supported by computed aromaticity indices (NICS, ACID, HOMA). Accordingly, substituents did not affect the fulfilment of the energetic criterion of SF, as the computed excited‐state energy levels satisfied the required E(S1)/E(T1) > 2 relationship. Further spectroscopic measurements revealed a concentration dependent quenching of the excited state and population of the S2 state on the nanosecond timescale, providing initial evidence for unusual photophysics and an alternative entry point for singlet fission with monobenzopentalenes.}, keywords = {substituent effect; substituent effects; Chromophores; excited states; EXCITED-STATES; Ground state; Photophysics; PHOTOPHYSICAL PROPERTIES; Excited state; ANTIAROMATICITY; bond length; pentalenes; singlet fission; pentalene; Material application; Singlet fissions; Molecular photonics; Symmetric structures}, year = {2024}, eissn = {1439-7641} } @article{MTMT:34450815, title = {Salicylideneaniline/Dithienylethene Hybrid Molecular Switches: Design, Synthesis, and Photochromism}, url = {https://m2.mtmt.hu/api/publication/34450815}, author = {Kalapos, Péter Pál and Kunfi, Attila and Bogner, Marcell M. and Holczbauer, Tamás and Kochman, Michał Andrzej and Durbeej, Bo and London, Gábor}, doi = {10.1021/acs.joc.3c00828}, journal-iso = {J ORG CHEM}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, volume = {89}, unique-id = {34450815}, issn = {0022-3263}, year = {2024}, eissn = {1520-6904}, pages = {16-26}, orcid-numbers = {Durbeej, Bo/0000-0001-5847-1196; London, Gábor/0000-0001-6078-3180} } @article{MTMT:34112865, title = {The π‐molecular complex of biphenylene and tetracyanoethylene}, url = {https://m2.mtmt.hu/api/publication/34112865}, author = {Dobszay, Rita and Mayer, Péter József and Holczbauer, Tamás and Kunfi, Attila and Stirling, András and London, Gábor}, doi = {10.1002/hlca.202300079}, journal-iso = {HELV CHIM ACTA}, journal = {HELVETICA CHIMICA ACTA}, volume = {106}, unique-id = {34112865}, issn = {0018-019X}, abstract = {The investigation of the biphenylene (BP)‐tetracyanoethylene (TCNE) π‐molecular complex is reported. The first study on this complex appeared in 1961 and was considered as a charge transfer complex with a symmetric, co‐planar arrangement of the components. Moreover, it was assumed that this arrangement is not only dictated by the formation of a Mulliken‐type donor‐acceptor complex, but also by the electronic stabilization of the “cyclobutadieneoid” central ring of biphenylene through complex formation. Yet, crystal structure and associated computational analysis have not verified these predictions so far. We found that factors other than charge‐transfer interactions are most influential in the crystal formation. The low association constant in solution, and the weak interaction between the components in the 1:1 crystal structure point towards the low contribution of charge transfer interactions to their binding. Nevertheless, the presence of these interaction is hinted by the color of its solution and verified by theoretical calculations. Furthermore, Nucleus Independent Chemical Shift (NICS) calculations were carried out to characterize potential changes in the (anti)aromatic character of BP upon complex formation. The NICS(0) values of the rings of BP exhibit tiny changes both in the BP‐TCNE dimer and in the crystal, which also suggests weak electronic interactions between them.}, year = {2023}, eissn = {1522-2675} } @article{MTMT:33735013, title = {Vertical π-extension of dibenzopentalene: a combined experimental and computational study of a phenanthreno-benzopentalene derivative}, url = {https://m2.mtmt.hu/api/publication/33735013}, author = {Mayer, Péter József and Botlik, Bence B. and Meiszter, Enikő and Németh, Krisztina and Schürmann, Christian J. and Holczbauer, Tamás and London, Gábor}, doi = {10.1016/j.comptc.2023.114113}, journal-iso = {COMPUT THEOR CHEM}, journal = {COMPUTATIONAL AND THEORETICAL CHEMISTRY}, volume = {1224}, unique-id = {33735013}, issn = {2210-271X}, year = {2023}, eissn = {2210-2728} } @article{MTMT:33565543, title = {Stable Monoareno-pentalenes with Two Olefinic Protons}, url = {https://m2.mtmt.hu/api/publication/33565543}, author = {Mayer, Péter József and London, Gábor}, doi = {10.1021/acs.orglett.2c03752}, journal-iso = {ORG LETT}, journal = {ORGANIC LETTERS}, volume = {25}, unique-id = {33565543}, issn = {1523-7060}, year = {2023}, eissn = {1523-7052}, pages = {42-46}, orcid-numbers = {Mayer, Péter József/0000-0003-4891-3119; London, Gábor/0000-0001-6078-3180} } @article{MTMT:33204119, title = {Metal-free synthesis of indenone derivatives from ortho -alkynylaryl ketones mediated by the combination of dialkyl phosphonates and CBr 4}, url = {https://m2.mtmt.hu/api/publication/33204119}, author = {Adorján, Áron and Mayer, Péter József and Szabó, Pál Tamás and Holczbauer, Tamás and London, Gábor}, doi = {10.1080/00397911.2022.2122725}, journal-iso = {SYNTHETIC COMMUN}, journal = {SYNTHETIC COMMUNICATIONS}, volume = {52}, unique-id = {33204119}, issn = {0039-7911}, year = {2022}, eissn = {1532-2432}, pages = {1956-1966}, orcid-numbers = {Szabó, Pál Tamás/0000-0003-2260-4641} } @article{MTMT:33003988, title = {Photoswitching of Local (Anti)Aromaticity in Biphenylene-Based Diarylethene Molecular Switches.}, url = {https://m2.mtmt.hu/api/publication/33003988}, author = {Kalapos, Péter Pál and Mayer, Péter József and Gazdag, Tamás and Demeter, Attila and Oruganti, Baswanth and Durbeej, Bo and London, Gábor}, doi = {10.1021/acs.joc.2c00504}, journal-iso = {J ORG CHEM}, journal = {JOURNAL OF ORGANIC CHEMISTRY}, volume = {87}, unique-id = {33003988}, issn = {0022-3263}, abstract = {Photoinduced tuning of (anti)aromaticity and associated molecular properties is currently in the focus of attention for both tailoring photochemical reactivity and designing new materials. Here, we report on the synthesis and spectroscopic characterization of diarylethene-based molecular switches embedded in a biphenylene structure composed of rings with different levels of local (anti)aromaticity. We show that it is possible to modulate and control the (anti)aromatic character of each ring through reversible photoswitching of the aryl units of the system between open and closed forms. Remarkably, it is shown that the irreversible formation of an annulated bis(dihydro-thiopyran) side-product that hampers the photoswitching can be efficiently suppressed when the aryl core formed by thienyl groups in one switch is replaced by thiazolyl groups in another.}, year = {2022}, eissn = {1520-6904}, pages = {9532-9542} }