nach oben

Erschienen in:

2022 | OriginalPaper | Buchkapitel

10. Organic Salts as Tectons for Self-assembly Processes in Solution

verfasst von : Salvatore Marullo, Carla Rizzo, Francesca D’Anna

Erschienen in: Supramolecular Assemblies Based on Electrostatic Interactions

Verlag: Springer International Publishing

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config

KI-gestützte Suche

Aus

Abstract

The literature, covering the last decade, about the self-assembly processes of organic salts in conventional solvents was analyzed. In particular, data reported about imidazolium and ammonium salts have been considered. The analysis shows that these processes are highly determined by structural features of the salts. Indeed, besides the nature of the cationic head, features of the alkyl chain borne on the cation structure and its possible functionalization, as well as the nature of the anion play a pivotal role. These factors determine not only the nature of the solvent in which the process occurs but also the nature of the self-assembly mechanism. Consequently, the structure tunability of the salts affects the characteristics of the aggregates and, in turn, their possible applications. To this aim, some interesting applications in the biomedical field are reviewed and discussed.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Vorheriges Kapitel Aqueous Supramolecular Assemblies of Photocontrolled Molecular Amphiphiles

Nächstes Kapitel Computational Modelling of Supramolecular Polymers

Regnault MV (1839) J Franklin Inst 27:2CrossRef

Salikolimi K, Sudhakar AA, Ishida Y (2020) Functional ionic liquid crystals. Langmuir 36(40):11702–11731CrossRef

Goossens K, Lava K, Bielawski CW, Binnemans K (2016) Ionic liquid crystals: versatile materials. Chem Rev (Washington, DC, US) 116(8):4643–4807

Samarkina DA, Gabdrakhmanov DR, Semenov VE, Valeeva FG, Gubaidullina LM, Zakharova LY, Reznik VS, Konovalov AI (2016) Self-assembling catalytic systems based on new amphiphile containing purine fragment, exhibiting substrate specificity in hydrolysis of phosphorus acids esters. Russ J Gen Chem 86(3):656–660CrossRef

Mirgorodskaya AB, Kushnazarova RA, Lukashenko SS, Zakharova LY (2019) Self-assembly of mixed systems based on nonionic and carbamate-bearing cationic surfactants as a tool for fabrication of biocompatible nanocontainers. J Mol Liq 292:111407

Hao J, Qin T, Zhang Y, Li Y, Zhang Y (2019) Synthesis, surface properties and antimicrobial performance of novel gemini pyridinium surfactants. Colloids Surf B 181:814–821CrossRef

Cancemi P, Buttacavoli M, D’Anna F, Feo S, Fontana RM, Noto R, Sutera A, Vitale P, Gallo G (2017) The effects of structural changes on the anti-microbial and anti-proliferative activities of diimidazolium salts. New J Chem 41(9):3574–3585CrossRef

Garcia MT, Ribosa I, Perez L, Manresa A, Comelles F (2013) Aggregation behavior and antimicrobial activity of ester-functionalized imidazolium- and pyridinium-based ionic liquids in aqueous solution. Langmuir 29(8):2536–2545CrossRef

Rizzo C, Arrigo R, Dintcheva NT, Gallo G, Giannici F, Noto R, Sutera A, Vitale P, D’Anna F (2017) Supramolecular hydro- and ionogels: a study of their properties and antibacterial activity. Chem Eur J 23(64):16297–16311CrossRef

10.

Lei J, Gao Y, Ma Y, Zhao K, Du F (2019) Improving the emulsion stability by regulation of dilational rheology properties. Colloids Surf A: Physicochem Eng Asp 583:123906

11.

Consorti CS, Suarez PAZ, de Souza RF, Burrow RA, Farrar DH, Lough AJ, Loh W, da Silva LHM, Dupont J (2005) Identification of 1,3-dialkylimidazolium salt supramolecular aggregates in solution. J Phys Chem B 109(10):4341–4349CrossRef

12.

D’Anna F, Marullo S, Vitale P, Noto R (2011) The effect of the cation π-surface area on the 3D organization and catalytic ability of imidazolium-based ionic liquids. Eur J Org Chem 28:5681–5689CrossRef

13.

Rizzo C, D’Anna F, Marullo S, Noto R (2014) Task specific dicationic ionic liquids: recyclable reaction media for the mononuclear rearrangement of heterocycles. J Org Chem 79(18):8678–8683CrossRef

14.

Rojas M, Santos JG, Orth E, Figueroa R, Pavez P (2020) The effect of imidazolium salts with amino acids as counterions on the reactivity of 4-nitrophenyl acetate: a kinetic study. J Mol Liq 310: 113206

15.

Zhu H, Vijayaraghavan R, MacFarlane DR, Forsyth M (2019) Self-assembled structure and dynamics of imidazolium-based protic salts in water solution. Phys Chem Chem Phys 21(5):2691–2696CrossRef

16.

Jiao J, Han B, Lin M, Cheng N, Yu L, Liu M (2013) Salt-free catanionic surface active ionic liquids 1-alkyl-3-methylimidazolium alkylsulfate: aggregation behavior in aqueous solution. J Colloid Interface Sci 412:24–30CrossRef

17.

Bai G, Wang J, Wang Y, Yan H, Thomas RK (2002) Thermodynamics of hydrophobic interaction of dissymmetric gemini surfactants in aqueous solutions. J Phys Chem B 106(26):6614–6616CrossRef

18.

Kuznetsova DA, Gabdrakhmanov DR, Kuznetsov DM, Lukashenko SS, Sapunova AS, Voloshina AD, Nizameev IR, Kadirov MK, Zakharova LY (2020) Biocompatible supramolecular systems based on novel cationic imidazolium- and urethane-containing amphiphiles: self-assembly and antimicrobial properties. J Mol Liq 319:114094

19.

Kuznetsova DA, Gabdrakhmanov DR, Ahtamyanova LR, Lukashenko SS, Kusova AM, Zuev YF, Voloshina AD, Sapunova AS, Kulik NV, Kuznetsov DM, Nizameev IR, Kadirov MK, Zakharova LY (2020) Novel self-assembling systems based on imidazolium amphiphiles with cleavable urethane fragment for construction of soft nanocontainers for biomedicine application. J Mol Liq 298:111961

20.

Garcia MT, Ribosa I, Perez L, Manresa A, Comelles F (2017) Micellization and antimicrobial properties of surface-active ionic liquids containing cleavable carbonate linkages. Langmuir 33(26):6511–6520CrossRef

21.

Samarkina DA, Gabdrakhmanov DR, Lukashenko SS, Khamatgalimov AR, Kovalenko VI, Zakharova LY (2017) Cationic amphiphiles bearing imidazole fragment: from aggregation properties to potential in biotechnologies. Colloids Surf A 529:990–997CrossRef

22.

Kuznetsova DA, Gabdrakhmanov DR, Lukashenko SS, Voloshina AD, Sapunova AS, Kulik NV, Nizameev IR, Kadirov MK, Kashapov RR, Zakharova LY (2019) Supramolecular systems based on cationic imidazole-containing amphiphiles bearing hydroxyethyl fragment: aggregation properties and functional activity. J Mol Liq 289:111058

23.

Ma H, Ke H, Wang T, Xiao J, Du N, Yu L (2017) Self-assembly of imidazolium-based surface active ionic liquids in aqueous solution: the role of different substituent group on aromatic counterions. J Mol Liq 240:556–563CrossRef

24.

Singh G, Singh G, Kang TS (2016) Micellization behavior of surface active ionic liquids having aromatic counterions in aqueous media. J Phys Chem B 120(6):1092–1105CrossRef

25.

Sun P, Shi L, Lu F, Zheng L (2016) Aggregation behavior of zwitterionic surface active ionic liquids with different counterions, cations, and alkyl chains. RSC Adv 6(33):27370–27377CrossRef

26.

Xu W, Wang T, Cheng N, Hu Q, Bi Y, Gong Y, Yu L (2015) Experimental and DFT studies on the aggregation behavior of imidazolium-based surface-active ionic liquids with aromatic counterions in aqueous solution. Langmuir 31(4):1272–1282CrossRef

27.

Zhang G, Zhu H, Chen M, Pietraszkiewicz M, Pietraszkiewicz O, Li H, Hao J (2018) Aggregation-induced emission of Eu^III complexes balanced with bulky and amphiphilic imidazolium cations in ethanol/water binary mixtures. Chem Eur J 24(59):15912–15920CrossRef

28.

Barrio JD, Liu J, Brady RA, Tan CS, Chiodini S, Ricci M, Fernández-Leiro R, Tsai CJ, Vasileiadi P, Di Michele L, Lairez D, Toprakcioglu C, Scherman OA (2019) Emerging two-dimensional crystallization of cucurbit[8]uril complexes: from supramolecular polymers to nanofibers. J Am Chem Soc 141(36):14021–14025

29.

D’Anna F, Rizzo C, Vitale P, Marullo S, Ferrante F (2017) Supramolecular complexes formed by dimethoxypillar[5]arenes and imidazolium salts: a joint experimental and computational investigation. New J Chem 41(21):12490–12505CrossRef

30.

Casal-Dujat L, Griffiths PC, Rodríguez-Abreu C, Solans C, Rogers S, Pérez-García L (2013) Nanocarriers from dicationic bis-imidazolium amphiphiles and their interaction with anionic drugs. J Mater Chem B 1(38):4963–4971

31.

González-Mendoza L, Escorihuela J, Altava B, Burguete MI, Luis SV (2015) Application of optically active chiral bis(imidazolium) salts as potential receptors of chiral dicarboxylate salts of biological relevance. Org Biomol Chem 13(19):5450–5459CrossRef

32.

D’Anna F, Marullo S, Lazzara G, Vitale P, Noto R (2015) Aggregation processes of perylene bisimide diimidazolium salts. Chem Eur J 21(42):14780–14790CrossRef

33.

Marullo S, Feroci M, Noto R, D’Anna F (2017) Insights into the anion effect on the self assembly of perylene bisimide diimidazolium salts. Dyes Pigments 146:54–65CrossRef

34.

Billeci F, D’Anna F, Marullo S, Noto R (2016) Self-assembly of fluorescent diimidazolium salts: tailor properties of the aggregates changing alkyl chain features. RSC Adv 6(64):59502–59512CrossRef

35.

Billeci F, D’Anna F, Chiarotto I, Feroci M, Marullo S (2017) The anion impact on the self-assembly of naphthalene diimide diimidazolium salts. New J Chem 41(22):13889–13901CrossRef

36.

Rizzo C, Marullo S, Feroci M, Accurso V, D'Anna F (2021) Insights into the effect of the spacer on the properties of imidazolium based AIE luminogens. Dyes Pigments 186:109035

37.

Rizzo C, Cancemi P, Mattiello L, Marullo S, D’Anna F (2020) Naphthalimide imidazolium-based supramolecular hydrogels as bioimaging and theranostic soft materials. ACS Appl Mater Interfaces 12(43):48442–48457CrossRef

38.

Lee H-Y, Hashizaki K, Diehn K, Raghavan SR (2013) Reverse self-assembly of lipid onions induced by gadolinium and calcium ions. Soft Matter 9(1):200–207CrossRef

39.

Coste M, Kotras C, Bessin Y, Gervais V, Dellemme D, Leclercq M, Fossépré M, Richeter S, Clément S, Surin M, Ulrich S (2021) 2021, Synthesis, self-assembly, and nucleic acid recognition of an acylhydrazone-conjugated cationic tetraphenylethene ligand. Eur J Org Chem 7:1123–1135CrossRef

40.

Qian Z, Yuan T, Wang Q (2018) Supramolecular hexagonal network based on a tritopic amine hydrochloride and a cucurbit[5]uril analogue. Res Chem Intermed 44(10):6445–6451CrossRef

41.

de Rooy SL, Das S, Li M, El-Zahab B, Jordan A, Lodes R, Weber A, Chandler L, Baker GA, Warner IM (2012) Ionically self-assembled, multi-luminophore one-dimensional micro- and nanoscale aggregates of thiacarbocyanine GUMBOS. J Phys Chem C 116(14):8251–8260

42.

Yoshii Y, Hoshino N, Takeda T, Moritomo H, Kawamata J, Nakamura T, Akutagawa T (2014) The formation of organogels and helical nanofibers from simple organic salts. Chem Eur J 20(49):16279–16285CrossRef

43.

Deng S-L, Zhao J-X, Wen Z-X (2018) Self-assembly of quaternary ammonium gemini surfactants in cyclohexane upon reinforcement by simple counterions. RSC Adv 8(34):18880–18888CrossRef

44.

Cui K, Mali KS, Ivasenko O, Wu D, Feng X, Walter M, Müllen K, De Feyter S, Mertens SFL (2014) Squeezing, then stacking: from breathing pores to three-dimensional ionic self-assembly under electrochemical control. Angew Chem Int Ed 53(47):12951–12954

45.

Zhu Q, Yang H, Li Y, Tian Y, Wang W, Tang W, Yuan Y, Hu A (2016) HP-DO3A-based amphiphilic MRI contrast agents and relaxation enhancement through their assembly with polyelectrolytes. J Mater Chem B 4(45):7241–7248CrossRef

46.

Zhou Y, Jie K (2017) A triply-responsive supramolecular amphiphile fabricated by a thermal-responsive pillar[5]arene-based host–guest recognition motif. Tetrahedron Lett 58(23):2217–2222CrossRef

47.

Zhao N, Li M, Yan Y, Lam JWY, Zhang YL, Zhao YS, Wong KS, Tang BZ (2013) A tetraphenylethene-substituted pyridinium salt with multiple functionalities: synthesis, stimuli-responsive emission, optical waveguide and specific mitochondrion imaging. J Mater Chem C 1(31):4640–4646CrossRef

48.

Hatakeda M, Toohara S, Nakashima T, Sakurai S, Kuroiwa K (2019) Helical-ribbon and tape formation of lipid packaged [Ru(bpy)₃]²⁺ complexes in organic media. Int J Mol Sci 20(13):3298CrossRef

49.

Niraula TP, Chatterjee SK, Bhattarai A (2018) Micellization of sodium dodecyl sulphate in presence and absence of alkali metal halides at different temperatures in water and methanol-water mixtures. J Mol Liq 250:287–294CrossRef

50.

He JH, Li CH, Qian LA, Liu JH, Zhang QL (2012) Self-assembly behavior of N-methly-N-hexadecyl-pyrrolidinium bromide in water. Adv Mater Res 557–559:611–614CrossRef

Titel: Organic Salts as Tectons for Self-assembly Processes in Solution
verfasst von: Salvatore Marullo
Carla Rizzo
Francesca D’Anna
Verlag: Springer International Publishing
Buch: Supramolecular Assemblies Based on Electrostatic Interactions
Print ISBN: 978-3-031-00656-2

Electronic ISBN: 978-3-031-00657-9

Copyright-Jahr: 2022
DOI: https://doi.org/10.1007/978-3-031-00657-9_10

Premium Partner

Marktübersichten

Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.

Zur Marktübersicht