{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,14]],"date-time":"2026-07-14T01:05:21Z","timestamp":1783991121657,"version":"3.55.0"},"reference-count":36,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2025,1,3]],"date-time":"2025-01-03T00:00:00Z","timestamp":1735862400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0"},{"start":{"date-parts":[[2025,1,3]],"date-time":"2025-01-03T00:00:00Z","timestamp":1735862400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0"}],"funder":[{"name":"National Office of Science, Innovation and Technology","award":["TKP2021-NVA-14"],"award-info":[{"award-number":["TKP2021-NVA-14"]}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Sci Rep"],"DOI":"10.1038\/s41598-024-84769-3","type":"journal-article","created":{"date-parts":[[2025,1,3]],"date-time":"2025-01-03T00:18:56Z","timestamp":1735863536000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivatives"],"prefix":"10.1038","volume":"15","author":[{"given":"Erika","family":"Kopcsik","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zolt\u00e1n","family":"Mucsi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rajmond","family":"Schiwert","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"L\u00e1szl\u00f3","family":"Vanyorek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"B\u00e9la","family":"Viskolcz","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mikl\u00f3s","family":"Nagy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2025,1,3]]},"reference":[{"key":"84769_CR1","doi-asserted-by":"publisher","first-page":"2345","DOI":"10.1021\/acs.energyfuels.6b02354","volume":"31","author":"D Chen","year":"2016","unstructured":"Chen, D. & Wang, H. Cation\u2009\u2013 \u03c0 interactions between Flame Chemi-ions and aromatic compounds. Energy Fuels 31, 2345\u20132352. https:\/\/doi.org\/10.1021\/acs.energyfuels.6b02354 (2016).","journal-title":"Energy Fuels"},{"key":"84769_CR2","doi-asserted-by":"publisher","unstructured":"Martinez, C. R. & Iverson, B. L. Rethinking the term pi-stacking. Chem. Sci. 3. https:\/\/doi.org\/10.1039\/c2sc20045g (2012).","DOI":"10.1039\/c2sc20045g"},{"key":"84769_CR3","doi-asserted-by":"publisher","unstructured":"Yang, S. Y., Qu, Y. K., Liao, L. S., Jiang, Z. Q. & Lee, S. T. Research Progress of Intramolecular \u03c0-Stacked small molecules for device applications. Adv. Mater. 34. https:\/\/doi.org\/10.1002\/adma.202104125 (2021).","DOI":"10.1002\/adma.202104125"},{"key":"84769_CR4","doi-asserted-by":"publisher","first-page":"17312","DOI":"10.1002\/anie.201910288","volume":"58","author":"CH Liu","year":"2019","unstructured":"Liu, C. H., Niazi, M. R. & Perepichka, D. F. Strong enhancement of \u03c0-Electron Donor\/Acceptor ability by complementary DD\/AA Hydrogen Bonding. Angew. Chem. Int. Ed. 58, 17312\u201317321. https:\/\/doi.org\/10.1002\/anie.201910288 (2019).","journal-title":"Angew. Chem. Int. Ed."},{"key":"84769_CR5","doi-asserted-by":"publisher","unstructured":"Roche, G. H. et al. \u03c0-Conjugated organosilica semiconductors: Toward robust organic electronics. Adv. Electron. Mater. 3. https:\/\/doi.org\/10.1002\/aelm.201700218 (2017).","DOI":"10.1002\/aelm.201700218"},{"key":"84769_CR6","doi-asserted-by":"publisher","first-page":"3663","DOI":"10.1039\/c9tc06608j","volume":"8","author":"W Wei","year":"2020","unstructured":"Wei, W. et al. Modulation of \u03c0-linkers in asymmetric thermally activated delayed fluorescence molecules enabling high performance OLEDs. J. Mater. Chem. C 8, 3663\u20133668. https:\/\/doi.org\/10.1039\/c9tc06608j (2020).","journal-title":"J. Mater. Chem. C"},{"key":"84769_CR7","doi-asserted-by":"publisher","first-page":"12740","DOI":"10.1039\/c9ta02636c","volume":"7","author":"S Liu","year":"2019","unstructured":"Liu, S. et al. Efficiency enhancement of organic photovoltaics by introducing high-mobility curved small-molecule semiconductors as additives. J. Mater. Chem. A 7, 12740\u201312750. https:\/\/doi.org\/10.1039\/c9ta02636c (2019).","journal-title":"J. Mater. Chem. A"},{"key":"84769_CR8","doi-asserted-by":"publisher","first-page":"919","DOI":"10.1021\/acs.jpclett.0c03526","volume":"12","author":"AK Hundal","year":"2021","unstructured":"Hundal, A. K. et al. Enhanced photovoltaic efficiency via control of self-assembly in cyanopyridone-based Oligothiophene Donors. J. Phys. Chem. Lett. 12, 919\u2013924. https:\/\/doi.org\/10.1021\/acs.jpclett.0c03526 (2021).","journal-title":"J. Phys. Chem. Lett."},{"key":"84769_CR9","doi-asserted-by":"publisher","first-page":"1654","DOI":"10.1021\/acs.accounts.7b00124","volume":"50","author":"J Zhang","year":"2017","unstructured":"Zhang, J., Xu, W., Sheng, P., Zhao, G. & Zhu, D. Organic donor\u2013acceptor complexes as novel organic semiconductors. Acc. Chem. Res. 50, 1654\u20131662. https:\/\/doi.org\/10.1021\/acs.accounts.7b00124 (2017).","journal-title":"Acc. Chem. Res."},{"key":"84769_CR10","doi-asserted-by":"publisher","first-page":"3421","DOI":"10.1021\/es8033044","volume":"43","author":"M Keiluweit","year":"2009","unstructured":"Keiluweit, M. & Kleber, M. Molecular-level interactions in soils and sediments: the role of aromatic \u03c0-Systems. Environ. Sci. Technol. 43, 3421\u20133429. https:\/\/doi.org\/10.1021\/es8033044 (2009).","journal-title":"Environ. Sci. Technol."},{"key":"84769_CR11","doi-asserted-by":"publisher","first-page":"265","DOI":"10.2134\/jeq2004.2650","volume":"33","author":"H Wijnja","year":"2004","unstructured":"Wijnja, H., Pignatello, J. J. & Malekani, K. Formation of \u03c0\u2013\u03c0 complexes between Phenanthrene and Model \u03c0-Acceptor Humic subunits. J. Environ. Qual. 33, 265\u2013275. https:\/\/doi.org\/10.2134\/jeq2004.2650 (2004).","journal-title":"J. Environ. Qual."},{"key":"84769_CR12","doi-asserted-by":"crossref","unstructured":"Sasidharan, S. & Ramakrishnan, V. In Protein Design and Structure Advances in Protein Chemistry and Structural Biology 119\u2013160 (2022).","DOI":"10.1016\/bs.apcsb.2022.01.001"},{"key":"84769_CR13","doi-asserted-by":"publisher","first-page":"386","DOI":"10.1021\/acs.cgd.7b01376","volume":"18","author":"MP Parker","year":"2017","unstructured":"Parker, M. P. et al. Mutual complexation between \u03c0\u2013\u03c0 stacked Molecular tweezers. Cryst. Growth Des. 18, 386\u2013392. https:\/\/doi.org\/10.1021\/acs.cgd.7b01376 (2017).","journal-title":"Cryst. Growth. Des."},{"key":"84769_CR14","doi-asserted-by":"publisher","first-page":"1017","DOI":"10.1021\/acs.inorgchem.7b02343","volume":"57","author":"E Aguil\u00f3","year":"2017","unstructured":"Aguil\u00f3, E. et al. Reversible self-assembly of Water-Soluble Gold(I) complexes. Inorg. Chem. 57, 1017\u20131028. https:\/\/doi.org\/10.1021\/acs.inorgchem.7b02343 (2017).","journal-title":"Inorg. Chem."},{"key":"84769_CR15","doi-asserted-by":"publisher","first-page":"8356","DOI":"10.1039\/d2cc02571j","volume":"58","author":"M Yoshida","year":"2022","unstructured":"Yoshida, M., Hirao, T. & Haino, T. Self-assembly of neutral platinum complexes controlled by thermal inputs. Chem. Commun. 58, 8356\u20138359. https:\/\/doi.org\/10.1039\/d2cc02571j (2022).","journal-title":"Chem. Commun."},{"key":"84769_CR16","unstructured":"Lehn, J. M. Supramolecular Chemistry: Concepts and Perspectives (Wiley, 2011)."},{"key":"84769_CR17","doi-asserted-by":"publisher","first-page":"5525","DOI":"10.1021\/ja00170a016","volume":"112","author":"CA Hunter","year":"2002","unstructured":"Hunter, C. A. & Sanders, J. K. M. The nature of.pi.-.Pi. Interactions. J. Am. Chem. Soc. 112, 5525\u20135534. https:\/\/doi.org\/10.1021\/ja00170a016 (2002).","journal-title":"J. Am. Chem. Soc."},{"key":"84769_CR18","doi-asserted-by":"publisher","first-page":"564","DOI":"10.1039\/b809359h","volume":"38","author":"Z Chen","year":"2009","unstructured":"Chen, Z., Lohr, A., Saha-Moller, C. R. & Wurthner, F. Self-assembled pi-stacks of functional dyes in solution: structural and thermodynamic features. Chem. Soc. Rev. 38, 564\u2013584. https:\/\/doi.org\/10.1039\/b809359h (2009).","journal-title":"Chem. Soc. Rev."},{"key":"84769_CR19","doi-asserted-by":"publisher","first-page":"254","DOI":"10.1002\/(SICI)1099-1395(199705)10:5<254::AID-POC875>3.0.CO;2-3","volume":"10","author":"CG Claessens","year":"1997","unstructured":"Claessens, C. G. & Stoddart, J. F. \u03c0-\u03c0 interactions in self-assembly. J. Phys. Org. Chem. 10, 254\u2013272 (1997).","journal-title":"J. Phys. Org. Chem."},{"key":"84769_CR20","doi-asserted-by":"publisher","first-page":"523","DOI":"10.1021\/acs.cgd.8b01630","volume":"19","author":"R Thakuria","year":"2019","unstructured":"Thakuria, R., Nath, N. K. & Saha, B. K. The nature and applications of \u03c0\u2013\u03c0 interactions: a perspective. Cryst. Growth Des. 19, 523\u2013528. https:\/\/doi.org\/10.1021\/acs.cgd.8b01630 (2019).","journal-title":"Cryst. Growth. Des."},{"key":"84769_CR21","doi-asserted-by":"publisher","first-page":"1898","DOI":"10.1021\/acs.cgd.0c01514","volume":"21","author":"JM \u017divkovi\u0107","year":"2021","unstructured":"\u017divkovi\u0107, J. M., Stankovi\u0107, I. M., Ninkovi\u0107, D. B. & Zari\u0107, S. D. Decisive Influence of Environment on Aromatic\/Aromatic Interaction Geometries. Comparison of Aromatic\/Aromatic Interactions in Crystal Structures of Small Molecules and in protein structures. Cryst. Growth. Des. 21, 1898\u20131904. https:\/\/doi.org\/10.1021\/acs.cgd.0c01514 (2021).","journal-title":"Cryst. Growth. Des."},{"key":"84769_CR22","doi-asserted-by":"publisher","first-page":"2925","DOI":"10.1007\/s11164-012-0849-6","volume":"39","author":"AK Tewari","year":"2013","unstructured":"Tewari, A. K., Srivastava, P., Singh, V. P., Singh, P. & Khanna, R. S. Molecular recognition phenomenon in aromatic compounds. Res. Chem. Intermediat. 39, 2925\u20132944. https:\/\/doi.org\/10.1007\/s11164-012-0849-6 (2013).","journal-title":"Res. Chem. Intermediat."},{"key":"84769_CR23","doi-asserted-by":"publisher","first-page":"5735","DOI":"10.1021\/ja909084e","volume":"132","author":"TF Headen","year":"2010","unstructured":"Headen, T. F. et al. Structure of pi-pi interactions in aromatic liquids. J. Am. Chem. Soc. 132, 5735\u20135742. https:\/\/doi.org\/10.1021\/ja909084e (2010).","journal-title":"J. Am. Chem. Soc."},{"key":"84769_CR24","doi-asserted-by":"publisher","first-page":"485","DOI":"10.1016\/0039-9140(81)80074-4","volume":"28","author":"K Verma","year":"1981","unstructured":"Verma, K. Detection of aromatic nitro compounds by means of their \u03c0-complexes with N,N-diethylaniline. Talanta 28, 485\u2013486. https:\/\/doi.org\/10.1016\/0039-9140(81)80074-4 (1981).","journal-title":"Talanta"},{"key":"84769_CR25","doi-asserted-by":"publisher","first-page":"5626","DOI":"10.1039\/c9py00929a","volume":"10","author":"E Kov\u00e1cs","year":"2019","unstructured":"Kov\u00e1cs, E. et al. Synthesis and supramolecular assembly of fluorinated biogenic amine recognition host polymers. Polym. Chem. 10, 5626\u20135634. https:\/\/doi.org\/10.1039\/c9py00929a (2019).","journal-title":"Polym. Chem."},{"key":"84769_CR26","doi-asserted-by":"publisher","first-page":"616815","DOI":"10.3389\/fchem.2021.616815","volume":"9","author":"M Levine","year":"2021","unstructured":"Levine, M. Fluorescence-based sensing of Pesticides using Supramolecular Chemistry. Front. Chem. 9, 616815. https:\/\/doi.org\/10.3389\/fchem.2021.616815 (2021).","journal-title":"Front. Chem."},{"key":"84769_CR27","doi-asserted-by":"publisher","first-page":"3614","DOI":"10.1002\/cphc.201402310","volume":"15","author":"M Nagy","year":"2014","unstructured":"Nagy, M. et al. Solvatochromic study of highly fluorescent Alkylated isocyanonaphthalenes, their \u03c0-Stacking, Hydrogen\u2010Bonding Complexation, and quenching with pyridine. ChemPhysChem 15, 3614\u20133625. https:\/\/doi.org\/10.1002\/cphc.201402310 (2014).","journal-title":"ChemPhysChem"},{"key":"84769_CR28","doi-asserted-by":"publisher","unstructured":"Nagy, M. et al. Antifungal activity of an original amino-isocyanonaphthalene (ICAN) compound family: promising broad spectrum antifungals. Molecules 25. https:\/\/doi.org\/10.3390\/molecules25040903 (2020).","DOI":"10.3390\/molecules25040903"},{"key":"84769_CR29","doi-asserted-by":"publisher","unstructured":"Szigeti, Z. M. et al. Potential original drug for Aspergillosis: In vitro and in vivo effects of 1-N,N-dimethylamino-5-isocyanonaphthalene (DIMICAN) on Aspergillus fumigatus. J. Fungi 8. https:\/\/doi.org\/10.3390\/jof8100985 (2022).","DOI":"10.3390\/jof8100985"},{"key":"84769_CR30","doi-asserted-by":"publisher","unstructured":"Kopcsik, E. et al. Preparation and optical study of 1-formamido-5-isocyanonaphthalene, the hydrolysis product of the potent antifungal 1,5-diisocyanonaphthalene. Int. J. Mol. Sci. 24. https:\/\/doi.org\/10.3390\/ijms24097780 (2023).","DOI":"10.3390\/ijms24097780"},{"key":"84769_CR31","doi-asserted-by":"publisher","unstructured":"Xiong, Z. et al. Reexamining the heavy-atom-effect: the universal heavy-atom-induced fluorescence enhancement principle for through-space conjugated AIEgens. Chem. Eng. J. 451. https:\/\/doi.org\/10.1016\/j.cej.2022.139030 (2023).","DOI":"10.1016\/j.cej.2022.139030"},{"key":"84769_CR32","doi-asserted-by":"publisher","first-page":"5389","DOI":"10.1021\/acs.analchem.9b00583","volume":"91","author":"K Nawara","year":"2019","unstructured":"Nawara, K. & Waluk, J. Goodbye to quinine in sulfuric acid solutions as a fluorescence quantum yield standard. Anal. Chem. 91, 5389\u20135394. https:\/\/doi.org\/10.1021\/acs.analchem.9b00583 (2019).","journal-title":"Anal. Chem."},{"key":"84769_CR33","doi-asserted-by":"crossref","unstructured":"Gaussian 16 Rev. C.01 (Wallingford, CT, 2016).","DOI":"10.5965\/1984723816322015001"},{"key":"84769_CR34","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1007\/s00214-007-0310-x","volume":"120","author":"Y Zhao","year":"2007","unstructured":"Zhao, Y. & Truhlar, D. G. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Acc. 120, 215\u2013241. https:\/\/doi.org\/10.1007\/s00214-007-0310-x (2007).","journal-title":"Theor. Chem. Acc."},{"key":"84769_CR35","doi-asserted-by":"publisher","first-page":"650","DOI":"10.1063\/1.438955","volume":"72","author":"R Krishnan","year":"1980","unstructured":"Krishnan, R., Binkley, J. S., Seeger, R. & Pople, J. A. Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J. Chem. Phys. 72, 650\u2013654. https:\/\/doi.org\/10.1063\/1.438955 (1980).","journal-title":"J. Chem. Phys."},{"key":"84769_CR36","doi-asserted-by":"publisher","first-page":"2999","DOI":"10.1021\/cr9904009","volume":"105","author":"J Tomasi","year":"2005","unstructured":"Tomasi, J., Mennucci, B. & Cammi, R. Quantum mechanical continuum solvation models. Chem. Rev. 105, 2999\u20133094. https:\/\/doi.org\/10.1021\/cr9904009 (2005).","journal-title":"Chem. Rev."}],"container-title":["Scientific Reports"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.nature.com\/articles\/s41598-024-84769-3.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-024-84769-3","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/www.nature.com\/articles\/s41598-024-84769-3.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,3]],"date-time":"2025-01-03T02:15:32Z","timestamp":1735870532000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.nature.com\/articles\/s41598-024-84769-3"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,1,3]]},"references-count":36,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2025,12]]}},"alternative-id":["84769"],"URL":"https:\/\/doi.org\/10.1038\/s41598-024-84769-3","relation":{"has-preprint":[{"id-type":"doi","id":"10.21203\/rs.3.rs-5152817\/v1","asserted-by":"object"}]},"ISSN":["2045-2322"],"issn-type":[{"value":"2045-2322","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,1,3]]},"assertion":[{"value":"25 September 2024","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"26 December 2024","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"3 January 2025","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Declarations"}},{"value":"A patent application under the number of P2400531 has been filed by the authors at the University of Miskolc.","order":2,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"629"}}