{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,19]],"date-time":"2026-09-19T08:55:44Z","timestamp":1789808144488,"version":"4.0.1"},"reference-count":20,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2022,9,2]],"date-time":"2022-09-02T00:00:00Z","timestamp":1662076800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["20-53-00043-Bel_a"],"award-info":[{"award-number":["20-53-00043-Bel_a"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["19-52-06004 MNTI_a"],"award-info":[{"award-number":["19-52-06004 MNTI_a"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["075-15-2021-677"],"award-info":[{"award-number":["075-15-2021-677"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002261","name":"Russian Foundation for Basic Research","doi-asserted-by":"publisher","award":["2.1.06.03"],"award-info":[{"award-number":["2.1.06.03"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002261","name":"RFBR and MOST project","doi-asserted-by":"publisher","award":["20-53-00043-Bel_a"],"award-info":[{"award-number":["20-53-00043-Bel_a"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002261","name":"RFBR and MOST project","doi-asserted-by":"publisher","award":["19-52-06004 MNTI_a"],"award-info":[{"award-number":["19-52-06004 MNTI_a"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002261","name":"RFBR and MOST project","doi-asserted-by":"publisher","award":["075-15-2021-677"],"award-info":[{"award-number":["075-15-2021-677"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002261","name":"RFBR and MOST project","doi-asserted-by":"publisher","award":["2.1.06.03"],"award-info":[{"award-number":["2.1.06.03"]}],"id":[{"id":"10.13039\/501100002261","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Ministry of Science and Higher Education RF","award":["20-53-00043-Bel_a"],"award-info":[{"award-number":["20-53-00043-Bel_a"]}]},{"name":"Ministry of Science and Higher Education RF","award":["19-52-06004 MNTI_a"],"award-info":[{"award-number":["19-52-06004 MNTI_a"]}]},{"name":"Ministry of Science and Higher Education RF","award":["075-15-2021-677"],"award-info":[{"award-number":["075-15-2021-677"]}]},{"name":"Ministry of Science and Higher Education RF","award":["2.1.06.03"],"award-info":[{"award-number":["2.1.06.03"]}]},{"name":"State Program of Scientific Researchers of Belarus","award":["20-53-00043-Bel_a"],"award-info":[{"award-number":["20-53-00043-Bel_a"]}]},{"name":"State Program of Scientific Researchers of Belarus","award":["19-52-06004 MNTI_a"],"award-info":[{"award-number":["19-52-06004 MNTI_a"]}]},{"name":"State Program of Scientific Researchers of Belarus","award":["075-15-2021-677"],"award-info":[{"award-number":["075-15-2021-677"]}]},{"name":"State Program of Scientific Researchers of Belarus","award":["2.1.06.03"],"award-info":[{"award-number":["2.1.06.03"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A concept of piezo-responsive hydrogen-bonded \u03c0-\u03c0-stacked organic frameworks made from Knoevenagel-condensed vanillin\u2013barbiturate conjugates was proposed. Replacement of the substituent at the ether oxygen atom of the vanillin moiety from methyl (compound 3a) to ethyl (compound 3b) changed the appearance of the products from rigid rods to porous structures according to optical microscopy and scanning electron microscopy (SEM), and led to a decrease in the degree of crystallinity of corresponding powders according to X-ray diffractometry (XRD). Quantum chemical calculations of possible dimer models of vanillin\u2013barbiturate conjugates using density functional theory (DFT) revealed that \u03c0-\u03c0 stacking between aryl rings of the vanillin moiety stabilized the dimer to a greater extent than hydrogen bonding between carbonyl oxygen atoms and amide hydrogen atoms. According to piezoresponse force microscopy (PFM), there was a notable decrease in the vertical piezo-coefficient upon transition from rigid rods of compound 3a to irregular-shaped aggregates of compound 3b (average values of d33 coefficient corresponded to 2.74 \u00b1 0.54 pm\/V and 0.57 \u00b1 0.11 pm\/V), which is comparable to that of lithium niobate (d33 coefficient was 7 pm\/V).<\/jats:p>","DOI":"10.3390\/molecules27175659","type":"journal-article","created":{"date-parts":[[2022,9,7]],"date-time":"2022-09-07T01:51:57Z","timestamp":1662515517000},"page":"5659","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Piezo-Responsive Hydrogen-Bonded Frameworks Based on Vanillin-Barbiturate Conjugates"],"prefix":"10.3390","volume":"27","author":[{"given":"Anna S.","family":"Nebalueva","sequence":"first","affiliation":[{"name":"Infochemistry Scientific Center, ITMO University, 191002 St. Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexandra A.","family":"Timralieva","sequence":"additional","affiliation":[{"name":"Infochemistry Scientific Center, ITMO University, 191002 St. Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9598-4839","authenticated-orcid":false,"given":"Roman V.","family":"Sadovnichii","sequence":"additional","affiliation":[{"name":"Infochemistry Scientific Center, ITMO University, 191002 St. Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9913-5324","authenticated-orcid":false,"given":"Alexander S.","family":"Novikov","sequence":"additional","affiliation":[{"name":"Infochemistry Scientific Center, ITMO University, 191002 St. Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3361-6947","authenticated-orcid":false,"given":"Mikhail V.","family":"Zhukov","sequence":"additional","affiliation":[{"name":"Infochemistry Scientific Center, ITMO University, 191002 St. Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aleksandr S.","family":"Aglikov","sequence":"additional","affiliation":[{"name":"Infochemistry Scientific Center, ITMO University, 191002 St. Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2245-3460","authenticated-orcid":false,"given":"Anton A.","family":"Muravev","sequence":"additional","affiliation":[{"name":"Infochemistry Scientific Center, ITMO University, 191002 St. Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tatiana V.","family":"Sviridova","sequence":"additional","affiliation":[{"name":"Chemistry Department, Belarussian State University, 220030 Minsk, Belarus"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6038-0872","authenticated-orcid":false,"given":"Vadim P.","family":"Boyarskiy","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, St. Petersburg State University, 198504 St. Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrei L.","family":"Kholkin","sequence":"additional","affiliation":[{"name":"Institute of Natural Sciences and Mathematics, Ural Federal University, 260026 Yekaterinburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ekaterina V.","family":"Skorb","sequence":"additional","affiliation":[{"name":"Infochemistry Scientific Center, ITMO University, 191002 St. Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,9,2]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2100864","DOI":"10.1002\/advs.202100864","article-title":"Piezoelectric materials for energy harvesting and sensing applications: Roadmap for future smart materials","volume":"8","author":"Mahapatra","year":"2021","journal-title":"Adv. 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Horiz."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1486","DOI":"10.1002\/(SICI)1521-3773(20000417)39:8<1486::AID-ANIE1486>3.0.CO;2-K","article-title":"Piezoelectricity in polar supramolecular materials","volume":"39","author":"Pralle","year":"2000","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"235703","DOI":"10.1088\/0957-4484\/21\/23\/235703","article-title":"Local piezoelectric properties of ZnO thin films prepared by RF-plasma-assisted pulsed-laser deposition method","volume":"21","author":"Bdikin","year":"2010","journal-title":"Nanotechnology"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2008452","DOI":"10.1002\/adma.202008452","article-title":"Construction of bio-piezoelectric platforms: From structures and synthesis to applications","volume":"33","author":"Xu","year":"2021","journal-title":"Adv. Mater."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1038\/nmat5045","article-title":"Control of piezoelectricity in amino acids by supramolecular packing","volume":"17","author":"Guerin","year":"2018","journal-title":"Nat. Mater."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"13566","DOI":"10.1038\/ncomms13566","article-title":"Self-assembly of diphenylalanine peptide with controlled polarization for power generation","volume":"7","author":"Nguyen","year":"2016","journal-title":"Nat. Commun."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Dishon, S., Ushakov, A., Nuraeva, A., Ehre, D., Lahav, M., Shur, V., Kholkin, A., and Lubomirsky, I. (2020). Surface piezoelectricity and pyroelectricity in centrosymmetric materials: A case of \u03b1-glycine. Materials, 13.","DOI":"10.3390\/ma13204663"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"16603","DOI":"10.1002\/chem.202002947","article-title":"Melamine\u2013barbiturate supramolecular assembly as a pH-dependent organic radical trap material","volume":"26","author":"Shilovskikh","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"8997","DOI":"10.1002\/chem.202001344","article-title":"Effect of an aromatic solvent on hydrogen-bond-directed supramolecular polymerization leading to distinct topologies","volume":"26","author":"Isobe","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1281","DOI":"10.1039\/D1SC06246H","article-title":"Fluorescent supramolecular polymers of barbiturate dyes with thiophene-cored twisted \u03c0-systems","volume":"13","author":"Kawaura","year":"2022","journal-title":"Chem. Sci."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"13216","DOI":"10.1039\/C8CC07853J","article-title":"Mechanochemical carbon\u2013carbon bond formation that proceeds via a cocrystal intermediate","volume":"54","author":"Lukin","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"32207","DOI":"10.1039\/C4RA03413A","article-title":"Reaction of 6-aminouracils with aldehydes in water as both solvent and reactant under FeCl3\u00b76H2O catalysis: Towards 5-alkyl\/arylidenebarbituric acid","volume":"4","author":"Lukin","year":"2014","journal-title":"RSC Adv."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1002\/wcms.81","article-title":"The ORCA program system","volume":"2","author":"Neese","year":"2012","journal-title":"Wiley Interdiscip. Rev. Comput. Mol. Sci."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"1740","DOI":"10.1002\/jcc.10318","article-title":"An improvement of the resolution of the identity approximation for the formation of the Coulomb matrix","volume":"24","author":"Neese","year":"2003","journal-title":"J. Comput. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2102524","DOI":"10.1002\/adfm.202102524","article-title":"2D layered dipeptide crystals for piezoelectric applications","volume":"31","author":"Zelenovskii","year":"2021","journal-title":"Adv. Funct. Mater."},{"key":"ref_20","unstructured":"(2022, April 21). Gwyddion. Available online: http:\/\/www.gwyddion.net."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/17\/5659\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:22:21Z","timestamp":1760142141000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/17\/5659"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,9,2]]},"references-count":20,"journal-issue":{"issue":"17","published-online":{"date-parts":[[2022,9]]}},"alternative-id":["molecules27175659"],"URL":"https:\/\/doi.org\/10.3390\/molecules27175659","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,9,2]]}}}