Abstract
Low-molecular-weight gels have great potential for use in a variety of fields, including petrochemicals, healthcare, and tissue engineering. These supramolecular gels are frequently metastable, implying that their properties are kinetically controlled to some extent. Here, we report on the in situ supramolecular gel formation by mixing 1,3-cyclohexane diamine (1) and isocyanate derivative (2) without any catalysis at room temperature in various organic solvents. A mixture of building blocks 1 and 2 in various organic solvents, dichloromethane, tetrahydrofuran, chloroform, toluene, and 1,4-dioxane, resulted in the stable formation of supramolecular gel at room temperature within 60–100 s. This gel formation was caused by the generation of urea moieties, which allows for the formation of intermolecular hydrogen-bonding interactions via reactions 1 and 2. In situ supramolecular gels demonstrated a typical entangled fiber structure with a width of 600 nm and a length of several hundred μm. In addition, the supramolecular gels were thermally reversible by heating and cooling. The viscoelastic properties of supramolecular gels in strain and frequency sweets were enhanced by increasing the concentration of a mixed 1 and 2. Furthermore, the supramolecular gels displayed a thixotropic effect, indicating a thermally reversible gel.
Highlights
Gels are recognized as soft materials with a wide range of applications in cosmetics, pharmaceuticals, and the food industry [1]
Gelled materials are colloidal systems made up of two coexisting phases: a liquid-like phase and a solid network, with the latter preventing the liquid from flowing in bulk [2]
Gelators can be classified into two categories according to the force driving their molecular aggregation: hydrogen-bondbased gelators [23–26] and non-hydrogen-bond-based gelators [27,28] (Figure 1)
Summary
Gels are recognized as soft materials with a wide range of applications in cosmetics, pharmaceuticals, and the food industry [1]. There has been a greater emphasis placed on understanding the self-assembly and subsequent behavior of these materials [3]. The results from these studies are used to design carefully tailored gel materials for diverse applications from tissue engineering [4–7] to nanoscale electronics [8–12]. Aliphatic amide [29] or urea-coupled cyclohexane [30], peptides [31–34], and sugar-based derivatives with distinct helical structures [35–37] are typical examples of the former [38–42]. An intermolecular hydrogen-bonding interaction was utilized to prepare helical supramolecular gels. Polymers 2022, 14, x Polymers 2022, 14, 400 utilized to prepare helical supramolecular gels. L. Feringa and Hanabusa tghraotuepnsarnetpioomrteerdicthSa, tS-e,noarnRti,oRm-1e,r2ic-cSy,clSo-h, eoxraRn,eRd-e1r,2iv-cayticvloeshepxoasnseesdsienrgivtawtivoeusrepaosmseosiseitniegs ftowromuedreoarmgaonieotgieeslsfoatrmloewd coorngcaennotgrealtsioantslo[4w6–c4o9n]c. RReeaaccttiioonn pprroocceessss ttoo ffoorrmm iinn ssiittuu ssuupprraammoolleeccuullaarr ggeell bbyy mmiixxeedd ccoommppoouunnddss 11 aanndd. Idnroagdedlist.ioInn,atdhdeyitidoenm, tohnesytrdaetemdotnhsattraintesdittuhacat tianlyssitius ocfatthaleyfsoisrmofattihoenfoofrmgealtaitoonr omfogleelcautolers cmanoleaccucelelesrcaaten tahcecefloerrmataetitohne ofofrsmuaptrioamn oolfescuuplarramhyodlercouglealrs,hwydhriochgedlsr,awsthiciaclhlyderanshtaicnaclleyd tehnehiranrecesudlttihnegirmreescuhlatinnigcaml pecrhoapneirctaielsp. rDop. eJ.rtAieds.amD.sJe. tAadl.a[m65s]erteaplo. r[t6e5d] rgeeplofrotremd agteiol nfobr-y emxaptlioointinbgy dexypnlaomitiincgcodvyanlaemnticchceomvailsetnryt cwhhemeriesttrhyewsihmeprelethmeisxiimngploefmamixiinneg aonf damalidneehayndde uanlddeehrywdeenut nimdeinrwe benotndimfoinrembaotinodn froearmctaiotinonanrdeatchteiorenbayngdeltahteiorenboyccguerlast.iTonheoyccinutrrso.dTuhceeyd tihnetrroedduocxe-dretshpeornesdiovxe-rheysdproongseivl esyhsytedmroginecl osrypstoermatiinngcomrpeotaral tiionngsminetgaelliomnesdiina.geHl omweedviae.r, ogHmneoollsywleiacenuvflseeairwtr,uogenwexllaysimthainpofulesewtistuthehxaweavinmethebpeoeldueestnfohtrhraeevpaednoderbteeietdedinofntorhaeralpatocdaardlttleaiotdlwiyotsnhfisoaalrtoactrhallhteoaewflayotsrfioimnsrgaot.thrioAehnfseoaoartfmirnseaugst.piuoArlnats,mosafotuslreudecspyuurilnlaat-g,r (sGsthatrcscmsocmaaT1hoeuoodythaycnrhe)ulelniopgucsdedadtlnveadotlhcamrstfireefeeniearrtoye(nHeooHocmni2dedinmdri(iogrusnnl)tecs1mietm.tan.enilerosrb)grrrsatnGeaIs,hlgyaealyiaoarnfoeito-tiitsn.e-ntcintbnhpcilhtnauioolaygov,uhodo,eyssnpdwbfaenetenlnwshdohmarndsneieidesiarfor,rsetwetaipmoomowemitrrftgdsnirrcercegaebobetaeeemayoigphssewensllltdpenpalfoaynictaeirn,f-ooegnowennru-eoacttrrtknbeacitliuihssriuoetnaceisttiovsmselnineewn,artrieaenvansenealemasmdrrddtaeiodactieptitsilstieivftugibiesnyicunromitnrtpecetlro.osoigunsywsheslvendopT(uiublta2cikatisfoaieehhpnnyauptoen)utittrieeinrsttuerraivatpvsesaiccamiedisafereiiurereoamlmntotes.laasuibalpnrtyar,t(ccmooeotu2epmrt.ostwirslrmlar)ioirefoeetTbouolaamohhnmacdcltoylnhlctephuuelsitiiioteiccacnioeeeiallnonlbuihooiaatrngesnnfgfiusrlrtnncoetaesisuatboiguteegsrthirnlbrplatfhmr,sedrleooeuagaaaelrweilicoclbnarcsanesfrlfhkfroteietuhcllmoggnieiesasdoratoilofreimdgmhlctoocbnmutnnllhouteerolltcanetifeomhnnabfoehooiedsdsccntegnanutrnefuueitkehbsmseohtcpdaprlsioferyeonanebioraaardfvnbunramlrarttrpaebyesmnciicmgamosoodririuaehduttxeniomnnoncaeuiooaleeptldtlttlhutlddiraierwiorrlehxuosoaeecsnaaifvcu1eennctenuntmduofea,d(peirgg3lopo1orrleadoorsa-eargi1)nrfbcratfolnmoro,aruyelmab3iougdtoebdnncgcrnah-ufesncsuocleuietsdei(olckeygisalllloc1toehadruwsrctsie)rw(vnuchnereloip2gd(aoeunnexnt1alc)arnoarhevgldagh)uasdneacfifdreentmearcreibmcahnxtnoceem(norahlca2obetgaoodraducseon)illsedscolcosyeiusrfeeyelkai(cti.lciregn2nrncrvsmnosduwddvay)uttdTgere.eile(.ienidalnnael1abhnrmIadtyisrr---)tngoyeecr.. 2in. gMtaotecorinaclesnatnradtiMonetihs oddisscussed in detail
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