Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

• Alberto Rubin Pedrazzo,
• Fabrizio Caldera,
• Marco Zanetti,
• Silvia Lucia Appleton,
• Nilesh Kumar Dhakar and
• Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

• Alberto Rubin Pedrazzo Fabrizio Caldera Marco Zanetti Silvia Lucia Appleton Nilesh Kumar Dhakar Francesco Trotta Dipartimento di Chimica, Università degli Studi di Torino, Via Giuria 7, Torino 10125, Italy 10.3762/bjoc.16.127 Abstract Cyclodextrin nanosponges (CD-NS) are nanostructured

• . Polysaccharides and, among them, starch derivatives such as cyclodextrins (CD), have recently emerged as they are safe, of low cost and biodegradable. Cyclodextrin nanosponges (CD-NS) are crosslinked cyclodextrin polymers characterized by a nanosized three-dimensional network. The reactive hydroxy groups of CDs

• goal of this work was to obtain cyclodextrin nanosponges via a ball-milling-driven synthesis, having the same physicochemical characteristics as the material synthesized through the solvent-based approach. Among the various types of cyclodextrin nanosponges, we chose carbonate NS, synthesized with 1,1

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

• Monica Ferro,
• Franca Castiglione,
• Nadia Pastori,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2017, 13, 182–194, doi:10.3762/bjoc.13.21

• of Chemistry, University of Torino, Via Pietro Giuria 7, 10125 Torino, Italy 10.3762/bjoc.13.21 Abstract Two different formulations of cyclodextrin nanosponges (CDNS), obtained by polycondensation of β-cyclodextrin with ethylenediaminetetraacetic acid dianhydride (EDTAn), were treated with aqueous

• reported matched the information from powder X-ray diffraction profiles. Keywords: cross-polarization; cyclodextrin; ibuprofen; nanosponges; solid-state NMR; Introduction In the last ten years cyclodextrin nanosponges (CDNS) polymer materials received great attention as promising new materials in several

• ) was encapsulated in cyclodextrin nanosponges (CDNS) obtained by cross-linking of β-cyclodextrin with ethylenediaminetetraacetic acid dianhydride (EDTAn) in two different preparations: CDNS(1:4) and CDNS(1:8), where the 1:n notation indicates the CD to EDTAn molar ratio used for the synthesis. The

Polydisperse methyl β-cyclodextrin–epichlorohydrin polymers: variable contact time ¹³C CP-MAS solid-state NMR characterization

• Isabelle Mallard,
• Davy Baudelet,
• Franca Castiglione,
• Monica Ferro,
• Walter Panzeri,
• Enzio Ragg and
• Andrea Mele

Beilstein J. Org. Chem. 2015, 11, 2785–2794, doi:10.3762/bjoc.11.299

• , efficient and environmentally sustainable route to highly cross-linked, nanoporous polymers commonly referred to as cyclodextrin nanosponges. One of the most frequently used crosslinker for insoluble polymers is epichlorohydrin (EP). In this case, the reaction of β-CD with EP requires very strong alkaline

• cyclodextrin nanosponges [41]. A striking feature from the data in Table 2 is that the values of T1ρ for all the H atoms of the three polymers are basically the same, with no particular variation related to structure or the synthetic route. In particular, it seems that the imprinting process has no effect on

Anomalous diffusion of Ibuprofen in cyclodextrin nanosponge hydrogels: an HRMAS NMR study

• Monica Ferro,
• Franca Castiglione,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2014, 10, 2715–2723, doi:10.3762/bjoc.10.286

• .10.286 Abstract Ibuprofen sodium salt (IP) was encapsulated in cyclodextrin nanosponges (CDNS) obtained by cross-linking of β-cyclodextrin with ethylenediaminetetraacetic acid dianhydride (EDTAn) in two different preparations: CDNSEDTA 1:4 and 1:8, where the 1:n notation indicates the CD to EDTAn molar

• -linked polymers; cyclodextrin nanosponges; diffusion; HRMAS NMR spectroscopy; TEM; Introduction Cyclodextrin nanosponges (CDNS) are a novel, promising class of nanoporous, three-dimensional polymers with interesting properties of sorption of both organic and inorganic species [1][2][3]. Indeed, several

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• dialdehydes, epoxides, epichlorohydrin, diacyl chlorides, etc., the term cyclodextrin nanosponges were first used by DeQuan Li and Min Ma in 1998 [11] to indicate a cross-linked β-cyclodextrin with organic diisocyanates leading to an insoluble network that showed a very high inclusion constant with several

• cyclodextrin nanosponges that they revealed their full potential in other fields, particularly as drug carriers. Generally speaking, nanosponges are hyper-cross-linked cyclodextrins that can be obtained with α, β and γ cyclodextrins, either alone or as mixtures containing relevant amounts of linear dextrin

• elsewhere [14]. Here we simply wish to stress that primary hydroxy groups are mainly involved in the formation of a network as shown by FTIR–ATR, Raman and solid-state NMR analyses [15]. Moreover, the elastic properties of cyclodextrin nanosponges were determined by analysis of the spectral modification of

Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene

• Wenting Liang,
• Cheng Yang,
• Masaki Nishijima,
• Gaku Fukuhara,
• Tadashi Mori,
• Andrea Mele,
• Franca Castiglione,
• Fabrizio Caldera,
• Francesco Trotta and
• Yoshihisa Inoue

Beilstein J. Org. Chem. 2012, 8, 1305–1311, doi:10.3762/bjoc.8.149

• photochirogenesis to use pyromellitate-linked polymeric β- and γ-CDs, termed “cyclodextrin nanosponges” (CDNSs) [25][26][27][28][29][30][31][32][33], as sensitizing hosts for the enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z) [34][35][36][37] and (Z,Z)-1,3-cyclooctadiene (2ZZ) [38][39][40

• enantiodifferentiating photosensitization occurs not in the CD cavity but in the chiral polymer void of CDNS. Conclusion The pyromellitate-linked cyclodextrin nanosponges, employed for the first time as supramolecular reaction media for sensitizing the enantiodifferentiating photoisomerization of 1Z and 2ZZ, exhibited

• ). Enantiodifferentiating photoisomerizations of 1Z and 2ZZ sensitized by β- and γ-cyclodextrin nanosponges (CDNSs) cross linked by pyromellitic dianhydride (PDA). Representative enantiodifferentiating photosensitization of 1Z and 2ZZ with conventional and supramolecular photosensitizers. Enantiodifferentiating