{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T11:15:55Z","timestamp":1760267755379,"version":"build-2065373602"},"reference-count":37,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2021,2,6]],"date-time":"2021-02-06T00:00:00Z","timestamp":1612569600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP18H01968, JP19K05444, JP26107007, JP20H05863"],"award-info":[{"award-number":["JP18H01968, JP19K05444, JP26107007, JP20H05863"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Dipyrrolyldiketones are essential building units of anion-responsive \u03c0-electronic molecules and ion-pairing assemblies. Here, we demonstrated that they form complexes with CuII characterized by planar geometries. The solid-state stacking assembled structures, as revealed by single-crystal X-ray analysis, were modulated by the substitution of pyrrole units. The rectangular shapes of the CuII complexes resulted in the formation of mesophases upon introduction of aliphatic chains.<\/jats:p>","DOI":"10.3390\/molecules26040861","type":"journal-article","created":{"date-parts":[[2021,2,14]],"date-time":"2021-02-14T02:08:12Z","timestamp":1613268492000},"page":"861","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Supramolecular Assemblies of Dipyrrolyldiketone CuII Complexes"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3824-4986","authenticated-orcid":false,"given":"Yohei","family":"Haketa","sequence":"first","affiliation":[{"name":"Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9928-1655","authenticated-orcid":false,"given":"Hiromitsu","family":"Maeda","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,2,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Koch, N. (2015). Supramolecular Materials for Opto-Electronics, The Royal Society of Chemistry.","DOI":"10.1039\/9781782626947"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"420","DOI":"10.1246\/bcsj.20170434","article-title":"Dimension-Controlled \u03c0-Electronic Ion-Pairing Assemblies","volume":"91","author":"Haketa","year":"2018","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"757","DOI":"10.1039\/C9ME00183B","article-title":"First decade of \u03c0-electronic ion-pairing assemblies","volume":"5","author":"Haketa","year":"2020","journal-title":"Mol. Syst. Des. Eng."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"10079","DOI":"10.1002\/anie.201006356","article-title":"Oriented salts: Dimension-controlled charge-by-charge assemblies from planar receptor\u2013anion complexes","volume":"49","author":"Haketa","year":"2010","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"8896","DOI":"10.1021\/ja203880d","article-title":"Anion modules: Building blocks of supramolecular assemblies by combination with \u03c0-conjugated anion receptors","volume":"133","author":"Maeda","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"7016","DOI":"10.1002\/chem.201200951","article-title":"Ion materials comprising planar charged species","volume":"18","author":"Haketa","year":"2012","journal-title":"Chem. Eur. J."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1284","DOI":"10.1021\/ja312214a","article-title":"Cation modules as building blocks forming supramolecular assemblies with planar receptor-anion complexes","volume":"135","author":"Dong","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"14797","DOI":"10.1021\/ja4071333","article-title":"Ion-based materials derived from positively and negatively charged chloride complexes of \u03c0-conjugated molecules","volume":"135","author":"Dong","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1099","DOI":"10.1016\/j.ccr.2008.07.013","article-title":"The evolution of \u03b2-diketophenol ligands and related complexes","volume":"253","author":"Vigato","year":"2009","journal-title":"Coord. Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1016\/j.ccr.2017.11.007","article-title":"Recent developments in the metallo-supramolecular chemistry of oligo-\u03b2-diketonato ligands","volume":"375","author":"Brock","year":"2018","journal-title":"Coord. Chem. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2067","DOI":"10.1021\/cm00059a013","article-title":"Controlling intermolecular interactions between metallomesogens: Side-chain effects in discotic copper, palladium, and vanadyl bis(\u03b2-diketonates","volume":"7","author":"Zheng","year":"1995","journal-title":"Chem. Mater."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Ohta, K., Yokoyama, M., Kusubayashi, S., and Mikawa, H. (1980). Square-planar trans-Bis-(1-p-n-octylphenylbutane-1,3-dionato)copper(II), a new compound exhibiting three kinds of \u2018double melting\u2032 behaviour. J. Chem. Soc. Chem. Commun., 392\u2013393.","DOI":"10.1039\/C39800000392"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Ohta, K., Ishii, A., Yamamoto, I., and Matsuzaki, K. (1984). Discotic liquid crystals of organocopper complexes: The substituent effects. J. Chem. Soc. Chem. Commun., 1099\u20131101.","DOI":"10.1039\/c39840001099"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1080\/10587259208028730","article-title":"Liquid-crystalline polymesomorphism in copper(II) complexes of \u03b2-diketones","volume":"213","author":"Thompson","year":"1992","journal-title":"Mol. Cryst. Liq. Cryst."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1080\/02678299408036539","article-title":"Discotic metallomesogens: Synthesis and properties of square planar metal bis(\u03b2-diketonate) complexes","volume":"16","author":"Poelsma","year":"1994","journal-title":"Liq. Cryst."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1080\/10587259508030997","article-title":"Liquid crystalline behaviour in some homologous series of \u03b2-diketones and a few of their copper(II) and palladium(II) complexes","volume":"268","author":"Prasad","year":"1995","journal-title":"Mol. Cryst. Liq. Cryst."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"12802","DOI":"10.1021\/acs.inorgchem.0c01846","article-title":"Dipyrrolyldiketonato Titanium(IV) complexes from monomeric to multinuclear architectures: Synthesis, stability and liquid crystal properties","volume":"59","author":"Schmidt","year":"2020","journal-title":"Inorg. Chem."},{"key":"ref_18","unstructured":"PtII complexes of dipyrrolyldiketones have also been prepared and will be reported elsewhere."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1039\/B718317H","article-title":"BF2 complexes of \u03b1-alkyl-substituted dipyrrolyldiketones as acyclic anion receptors","volume":"6","author":"Maeda","year":"2008","journal-title":"Org. Biomol. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2612","DOI":"10.1021\/jo062660d","article-title":"BF2 Complexes of \u03b2-tetraethyl-substituted dipyrrolyldiketones as anion receptors: Potential building subunits for oligomeric systems","volume":"72","author":"Maeda","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"13661","DOI":"10.1021\/ja074435z","article-title":"Aryl-substituted C3-bridged oligopyrroles as anion receptors for formation of supramolecular organogels","volume":"129","author":"Maeda","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"208","DOI":"10.1246\/cl.2009.208","article-title":"Alkoxy-substituted derivatives of \u03c0-conjugated acyclic anion receptors: Effects of substituted positions","volume":"38","author":"Maeda","year":"2009","journal-title":"Chem. Lett."},{"key":"ref_23","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2013). Gaussian 09, Gaussian, Inc.. revision D.01."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Yang, L., Powell, D.R., and Houser, R.P. (2007). Structural variation in copper(I) complexes with pyridylmethylamide ligands: Structural analysis with a new four-coordinate geometry index, \u03c44. Dalton Trans., 955\u2013964.","DOI":"10.1039\/B617136B"},{"key":"ref_25","unstructured":"Turner, M.J., McKinnon, J.J., Wolff, S.K., Grimwood, D.J., Spackman, P.R., Jayatilaka, D., and Spackman, M.A. (2017). CrystalExplorer17, University of Western Australia."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"627","DOI":"10.1107\/S0108768104020300","article-title":"Novel tools for visualizing and exploring intermolecular interactions in molecular crystals","volume":"60","author":"McKinnon","year":"2004","journal-title":"Acta Crystallogr. Sect. B"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1107\/S2056989019001129","article-title":"Utilizing Hirshfeld surface calculations, non-covalent interaction (NCI) plots and the calculation of interaction energies in the analysis of molecular packing","volume":"75","author":"Tan","year":"2019","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_28","unstructured":"Similar characteristic Hirshfeld surfaces were observed in the crystal-state \u03c0\u2013\u03c0 stacking structures of large aromatic hydrocarbons such as hexabenzocoronene: See also [26]."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Tiekink, E.R.T., and Zukerman-Schpector, J. (2012). The importance of Pi-Interactions in Crystal Engineering: Frontiers in Crystal Engineering, Wiley.","DOI":"10.1002\/9781119945888"},{"key":"ref_30","unstructured":"For the elucidation of the mesophase structures: Ohta, K (2020). Physics and Chemistry of Molecular Assemblies, World Scientific."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"3692","DOI":"10.1055\/s-0036-1588780","article-title":"Synthesis of 5-arylpyrrole-2-carboxylic acids as key intermediates for nbd series hiv-1-entry inhibitors","volume":"49","author":"Belov","year":"2017","journal-title":"Synthesis"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"4432","DOI":"10.1039\/C9SM00846B","article-title":"Ionic N-phenylpyridinium tetracatenar mesogens: Competing driving forces in mesophase formation and unprecedented difference in phase stabilization within a homologous series","volume":"15","author":"Herod","year":"2019","journal-title":"Soft Matter"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"350","DOI":"10.1002\/asia.200600379","article-title":"Micro- and nanometer-scale porous, fibrous, and sheet architectures constructed by supramolecular assemblies of dipyrrolyldiketones","volume":"2","author":"Maeda","year":"2007","journal-title":"Chem. Asian J."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"Crystal structure refinement with SHELXL","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. Sect. A"},{"key":"ref_35","unstructured":"(2001). Yadokari-XG, Software for Crystal Structure Analyses."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"218","DOI":"10.5940\/jcrsj.51.218","article-title":"Release of software (Yadokari-XG 2009) for crystal structure analyses","volume":"51","author":"Kabuto","year":"2009","journal-title":"J. Cryst. Soc. Jpn."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1107\/S090744490804362X","article-title":"Structure validation in chemical crystallography","volume":"65","author":"Spek","year":"2009","journal-title":"Acta Crystallogr. Sect. D"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/4\/861\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:20:29Z","timestamp":1760160029000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/4\/861"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,2,6]]},"references-count":37,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2021,2]]}},"alternative-id":["molecules26040861"],"URL":"https:\/\/doi.org\/10.3390\/molecules26040861","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2021,2,6]]}}}