{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T01:54:04Z","timestamp":1785894844958,"version":"3.56.0"},"reference-count":64,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2024,5,5]],"date-time":"2024-05-05T00:00:00Z","timestamp":1714867200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Icelandic Research Fund Rann\u00eds Iceland","award":["IRF-228902-051"],"award-info":[{"award-number":["IRF-228902-051"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>We modified C3-symmetric benzene-1,3,5-tris-amide (BTA) by introducing flexible linkers in order to generate an N-centered BTA (N-BTA) molecule. The N-BTA compound formed gels in alcohols and aqueous mixtures of high-polar solvents. Rheological studies showed that the DMSO\/water (1:1, v\/v) gels were mechanically stronger compared to other gels, and a similar trend was observed for thermal stability. Powder X-ray analysis of the xerogel obtained from various aqueous gels revealed that the packing modes of the gelators in these systems were similar. The stimuli-responsive properties of the N-BTA towards sodium\/potassium salts indicated that the gel network collapsed in the presence of more nucleophilic anions such as cyanide, fluoride, and chloride salts at the MGC, but the gel network was intact when in contact with nitrate, sulphate, acetate, bromide, and iodide salts, indicating the anion-responsive properties of N-BTA gels. Anion-induced gel formation was observed for less nucleophilic anions below the MGC of N-BTA. The ability of N-BTA gels to act as an adsorbent for hazardous anionic and cationic dyes in water was evaluated. The results indicated that the ethanolic gels of N-BTA successfully absorbed methylene blue and methyl orange dyes from water. This work demonstrates the potential of the N-BTA gelator to act as a stimuli-responsive material and a promising candidate for water purification.<\/jats:p>","DOI":"10.3390\/molecules29092149","type":"journal-article","created":{"date-parts":[[2024,5,6]],"date-time":"2024-05-06T14:26:11Z","timestamp":1715005571000},"page":"2149","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Supramolecular Gels Based on C3-Symmetric Amides: Application in Anion-Sensing and Removal of Dyes from Water"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0009-0009-4506-2268","authenticated-orcid":false,"given":"Geethanjali","family":"Kuppadakkath","sequence":"first","affiliation":[{"name":"Department of Chemistry, Science Institute, University of Iceland, Dunhagi 3, 107 Reykjav\u00edk, Iceland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1557-1354","authenticated-orcid":false,"given":"Sreejith Sudhakaran","family":"Jayabhavan","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Science Institute, University of Iceland, Dunhagi 3, 107 Reykjav\u00edk, Iceland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9741-2997","authenticated-orcid":false,"given":"Krishna K.","family":"Damodaran","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Science Institute, University of Iceland, Dunhagi 3, 107 Reykjav\u00edk, Iceland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,5,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"57","DOI":"10.2478\/cdem-2023-0004","article-title":"Environmental Contaminants of Emerging Concern: Occurrence and Remediation","volume":"28","author":"Prasad","year":"2023","journal-title":"Chem. Didact. Ecol. Metrol."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Feng, W., Deng, Y., Yang, F., Miao, Q., and Ngien, S.K. (2023). Systematic Review of Contaminants of Emerging Concern (CECs): Distribution, Risks, and Implications for Water Quality and Health. Water, 15.","DOI":"10.3390\/w15223922"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"113160","DOI":"10.1016\/j.ecoenv.2021.113160","article-title":"A critical review on the treatment of dye-containing wastewater: Ecotoxicological and health concerns of textile dyes and possible remediation approaches for environmental safety","volume":"231","author":"Ali","year":"2022","journal-title":"Ecotoxicol. Environ. Saf."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"e02711","DOI":"10.1016\/j.heliyon.2019.e02711","article-title":"Textile finishing dyes and their impact on aquatic environs","volume":"5","author":"Berradi","year":"2019","journal-title":"Heliyon"},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Alsukaibi, A.K.D. (2022). Various Approaches for the Detoxification of Toxic Dyes in Wastewater. Processes, 10.","DOI":"10.3390\/pr10101968"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"4497","DOI":"10.1039\/D1MA00354B","article-title":"Recent advances on the removal of dyes from wastewater using various adsorbents: A critical review","volume":"2","author":"Dutta","year":"2021","journal-title":"Mater. Adv."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"110587","DOI":"10.1016\/j.ecoenv.2020.110587","article-title":"An analysis of the versatility and effectiveness of composts for sequestering heavy metal ions, dyes and xenobiotics from soils and aqueous milieus","volume":"197","author":"Mudhoo","year":"2020","journal-title":"Ecotoxicol. Environ. Saf."},{"key":"ref_8","unstructured":"Muthu, S.S. (2021). Sustainable Technologies for Textile Wastewater Treatments, Woodhead Publishing."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"3615","DOI":"10.1002\/ejoc.200400723","article-title":"Design and Application of Self-Assembled Low Molecular Weight Hydrogels","volume":"2005","author":"Feringa","year":"2005","journal-title":"Eur. J. Org. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2080","DOI":"10.1039\/C3CS60224A","article-title":"Supramolecular gel phase crystallization: Orthogonal self-assembly under non-equilibrium conditions","volume":"43","author":"Kumar","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3686","DOI":"10.1039\/b926219a","article-title":"Anion-tuned supramolecular gels: A natural evolution from urea supramolecular chemistry","volume":"39","author":"Steed","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1039\/D3SM01301D","article-title":"Supramolecular gels\u2014A panorama of low-molecular-weight gelators from ancient origins to next-generation technologies","volume":"20","author":"Smith","year":"2024","journal-title":"Soft Matter"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"11047","DOI":"10.1021\/jacs.2c02096","article-title":"Personal Perspective on Understanding Low Molecular Weight Gels","volume":"144","author":"Adams","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"4226","DOI":"10.1039\/C6CS00124F","article-title":"Applying low-molecular weight supramolecular gelators in an environmental setting\u2014Self-assembled gels as smart materials for pollutant removal","volume":"45","author":"Okesola","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"109759","DOI":"10.1016\/j.matdes.2021.109759","article-title":"Anions-responsive supramolecular gels: A review","volume":"205","author":"Li","year":"2021","journal-title":"Mater. Des."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"5165","DOI":"10.1039\/D0CS01166E","article-title":"Stimuli responsive dynamic transformations in supramolecular gels","volume":"50","author":"Panja","year":"2021","journal-title":"Chem. Soc. Rev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"025","DOI":"10.1055\/s-0040-1722263","article-title":"Recent Advances on Supramolecular Gels: From Stimuli-Responsive Gels to Co-Assembled and Self-Sorted Systems","volume":"3","author":"Chu","year":"2021","journal-title":"Org. Mater."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"6546","DOI":"10.1039\/C6CS00435K","article-title":"Gels with sense: Supramolecular materials that respond to heat, light and sound","volume":"45","author":"Jones","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1039\/C1JM13205A","article-title":"Stimuli responsive gels based on low molecular weight gelators","volume":"22","author":"Yang","year":"2012","journal-title":"J. Mater. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"123858","DOI":"10.1016\/j.molliq.2023.123858","article-title":"A library of benzimidazole based amide and urea derivatives as supramolecular gelators\u2014A comparative study","volume":"395","author":"Patel","year":"2024","journal-title":"J. Mol. Liq."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"10258","DOI":"10.1021\/acsami.5b00814","article-title":"Efficient and Selective Removal of Dyes Using Imidazolium-Based Supramolecular Gels","volume":"7","author":"Cheng","year":"2015","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"552","DOI":"10.1002\/asia.201701632","article-title":"Supramolecular Gels Derived from the Salts of Variously Substituted Phenylacetic Acid and Dicyclohexylamine: Design, Synthesis, Structures, and Dye Adsorption","volume":"13","author":"Roy","year":"2018","journal-title":"Chem. Asian J."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"127289","DOI":"10.1016\/j.colsurfa.2021.127289","article-title":"A supramolecular gel made from an azobenzene-based phenylalanine derivative: Synthesis, self-assembly, and dye adsorption","volume":"628","author":"Li","year":"2021","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1633","DOI":"10.1021\/cm062672f","article-title":"pH-Responsive, Bolaamphiphile-Based Smart Metallo-Hydrogels as Potential Dye-Adsorbing Agents, Water Purifier, and Vitamin B12 Carrier","volume":"19","author":"Ray","year":"2007","journal-title":"Chem. Mater."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1165","DOI":"10.1021\/cm203727r","article-title":"Chemical and Mechano Responsive Metal\u2013Organic Gels of Bis(benzimidazole)-Based Ligands with Cd(II) and Cu(II) Halide Salts: Self Sustainability and Gas and Dye Sorptions","volume":"24","author":"Samai","year":"2012","journal-title":"Chem. Mater."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"4693","DOI":"10.1021\/jp500113h","article-title":"Hydrogels Facilitated by Monovalent Cations and Their Use as Efficient Dye Adsorbents","volume":"118","author":"Wang","year":"2014","journal-title":"J. Phys. Chem. B"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"39310","DOI":"10.1021\/acsomega.2c05466","article-title":"Sugar-Based Phase-Selective Supramolecular Self-Assembly System for Dye Removal and Selective Detection of Cu2+ Ions","volume":"7","author":"Bhavya","year":"2022","journal-title":"ACS Omega"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"11164","DOI":"10.1039\/c3cc45969a","article-title":"Versatile supramolecular pH-tolerant hydrogels which demonstrate pH-dependent selective adsorption of dyes from aqueous solution","volume":"49","author":"Okesola","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"138","DOI":"10.1016\/j.psep.2020.05.034","article-title":"Recent advances in the treatment of dye-containing wastewater from textile industries: Overview and perspectives","volume":"143","author":"Samsami","year":"2020","journal-title":"Process Saf. Environ. Prot."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Weiss, R.G., and Terech, P. (2006). Molecular Gels: Materials with Self-Assembled Fibrillar Networks, Springer.","DOI":"10.1007\/1-4020-3689-2"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1007\/b107172","article-title":"Systematic design of amide- and urea-type gelators with tailored properties","volume":"256","author":"Fages","year":"2005","journal-title":"Top. Curr. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"975","DOI":"10.1021\/acs.accounts.8b00536","article-title":"Triarylamine-Based Supramolecular Polymers: Structures, Dynamics, and Functions","volume":"52","author":"Moulin","year":"2019","journal-title":"Acc. Chem. Res."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3800","DOI":"10.1002\/anie.201812412","article-title":"Access to Metastable Gel States Using Seeded Self-Assembly of Low-Molecular-Weight Gelators","volume":"58","author":"Wang","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"122023","DOI":"10.1016\/j.molliq.2023.122023","article-title":"Structural modification induced hydrogelation and antibacterial properties in supramolecular gels","volume":"382","author":"Ghosh","year":"2023","journal-title":"J. Mol. Liq."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3517","DOI":"10.1021\/acs.chemmater.0c00475","article-title":"Unraveling the Self-Assembly Modes in Multicomponent Supramolecular Gels Using Single-Crystal X-ray Diffraction","volume":"32","author":"Ghosh","year":"2020","journal-title":"Chem. Mater."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2699","DOI":"10.1039\/b807346e","article-title":"Supramolecular gelling agents: Can they be designed?","volume":"37","author":"Dastidar","year":"2008","journal-title":"Chem. Soc. Rev."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1201","DOI":"10.1021\/cr0302049","article-title":"Water gelation by small organic molecules","volume":"104","author":"Estroff","year":"2004","journal-title":"Chem. Rev."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1039\/D0SM01804J","article-title":"The effect of amide bond orientation and symmetry on the self-assembly and gelation of discotic tripeptides","volume":"17","author":"Kumar","year":"2021","journal-title":"Soft Matter"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"126238","DOI":"10.1016\/j.colsurfa.2021.126238","article-title":"Effective adsorption of arsenate, dyes and eugenol from aqueous solutions by cationic supramolecular gel materials","volume":"616","author":"Yang","year":"2021","journal-title":"Colloids Surf. A Physicochem. Eng. Asp."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"108066","DOI":"10.1016\/j.dyepig.2019.108066","article-title":"A self-assembled supramolecular gel constructed by phenazine derivative and its application in ultrasensitive detection of cyanide","volume":"174","author":"Fang","year":"2020","journal-title":"Dyes Pigm."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1016\/j.reactfunctpolym.2017.11.003","article-title":"Design of folic acid based supramolecular hybrid gel with improved mechanical properties in NMP\/H2O for dye adsorption","volume":"122","author":"Hao","year":"2018","journal-title":"React. Funct. Polym."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"15420","DOI":"10.1038\/ncomms15420","article-title":"Dynamic diversity of synthetic supramolecular polymers in water as revealed by hydrogen\/deuterium exchange","volume":"8","author":"Lou","year":"2017","journal-title":"Nat. Commun."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1427","DOI":"10.1039\/C7CE00206H","article-title":"Benzene-1,3,5-tricarboxamide n-alkyl ester and carboxylic acid derivatives: Tuneable structural, morphological and thermal properties","volume":"19","author":"Lynes","year":"2017","journal-title":"CrystEngComm"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"4838","DOI":"10.1021\/nn305813y","article-title":"Chemical Nano-Gardens: Growth of Salt Nanowires from Supramolecular Self-Assembly Gels","volume":"7","author":"Daly","year":"2013","journal-title":"ACS Nano"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2332","DOI":"10.1021\/cm049881p","article-title":"Nonpolymeric Hydrogelators Derived from Trimesic Amides","volume":"16","author":"Kumar","year":"2004","journal-title":"Chem. Mater."},{"key":"ref_46","unstructured":"Goodwin, J.W., and Hughes, R.W. (2008). Rheology for Chemists: An Introduction, Royal Society of Chemistry."},{"key":"ref_47","unstructured":"Guenet, J.-M. (2016). Organogels: Thermodynamics, Structure, Solvent Role, and Properties, Springer."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"6697","DOI":"10.1039\/c3cs60080g","article-title":"Characterization of supramolecular gels","volume":"42","author":"Yu","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Adams, D.J. (2018). Does Drying Affect Gel Networks?. Gels, 4.","DOI":"10.3390\/gels4020032"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"8130","DOI":"10.1039\/C5CE00901D","article-title":"Selective gelation of N-(4-pyridyl)nicotinamide by copper(ii) salts","volume":"17","author":"Ghosh","year":"2015","journal-title":"CrystEngComm"},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Ghosh, D., Mulvee, M.T., and Damodaran, K.K. (2019). Tuning Gel State Properties of Supramolecular Gels by Functional Group Modification. Molecules, 24.","DOI":"10.3390\/molecules24193472"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1080\/10610278.2020.1751845","article-title":"Metal complexation induced supramolecular gels for the detection of cyanide in water","volume":"32","author":"Ghosh","year":"2020","journal-title":"Supramol. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1960","DOI":"10.1021\/cr9003067","article-title":"Metal- and Anion-Binding Supramolecular Gels","volume":"110","author":"Piepenbrock","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"83303","DOI":"10.1039\/C6RA16345A","article-title":"Anion responsive and morphology tunable tripodal gelators","volume":"6","author":"Ghosh","year":"2016","journal-title":"RSC Adv."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"e202300302","DOI":"10.1002\/cplu.202300302","article-title":"The Role of Functional Groups in Tuning the Self-Assembly Modes and Physical Properties of Multicomponent Gels","volume":"88","author":"Kuppadakkath","year":"2023","journal-title":"ChemPlusChem"},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Jayabhavan, S.S., Kristinsson, B., Ghosh, D., Breton, C., and Damodaran, K.K. (2023). Stimuli-Responsive Properties of Supramolecular Gels Based on Pyridyl-N-oxide Amides. Gels, 9.","DOI":"10.3390\/gels9020089"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"4662","DOI":"10.1039\/C9SM00656G","article-title":"Multi-stimuli-responsive hydrogels of gluconamide-tailored anthracene","volume":"15","author":"Zhang","year":"2019","journal-title":"Soft Matter"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"10270","DOI":"10.1039\/C8NJ05613G","article-title":"A sulfonyl hydrazone cholesterol conjugate: Gelation, anion interaction and its application in dye adsorption","volume":"43","author":"Panja","year":"2019","journal-title":"New J. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"2718","DOI":"10.1039\/C8NJ05626A","article-title":"A 1,8-naphthalimide\u2013pyridoxal conjugate as a supramolecular gelator for colorimetric read out of F\u2212 ions in solution, gel and solid states","volume":"43","author":"Pati","year":"2019","journal-title":"New J. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"2665","DOI":"10.1007\/s10311-022-01414-z","article-title":"Hydrogels for the removal of the methylene blue dye from wastewater: A review","volume":"20","author":"Yang","year":"2022","journal-title":"Environ. Chem. Lett."},{"key":"ref_61","first-page":"195","article-title":"Removal of toxic methyl orange by a cost-free and eco-friendly adsorbent: Mechanism, phytotoxicity, thermodynamics, and kinetics","volume":"40","author":"Dutta","year":"2022","journal-title":"S. Afr. J. Chem. Eng."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"100179","DOI":"10.1016\/j.crgsc.2021.100179","article-title":"Adsorption of methyl orange: A review on adsorbent performance","volume":"4","author":"Iwuozor","year":"2021","journal-title":"Curr. Res. Green Sustain. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","unstructured":"Fortunato, A., and Mba, M. (2022). A Peptide-Based Hydrogel for Adsorption of Dyes and Pharmaceuticals in Water Remediation. Gels, 8.","DOI":"10.3390\/gels8100672"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"17541","DOI":"10.1002\/chem.201404502","article-title":"Preparation of Thermocleavable Conjugates Based on Ansamitocin and Superparamagnetic Nanostructured Particles by a Chemobiosynthetic Approach","volume":"20","author":"Mancuso","year":"2014","journal-title":"Chem. Eur. J."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/9\/2149\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T14:39:59Z","timestamp":1760107199000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/9\/2149"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,5,5]]},"references-count":64,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2024,5]]}},"alternative-id":["molecules29092149"],"URL":"https:\/\/doi.org\/10.3390\/molecules29092149","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,5,5]]}}}