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Such compartmentalization offers a strategy for functional membrane materials because clustered molecules can exhibit properties that differ from those of uniformly mixed membranes. Despite this potential, the induction of thermally stable domains in fluid lipid bilayers remains a challenge owing to the high miscibility of lipid molecules. Here, we report triptycene-based lipid mimics that induce thermally stable membrane phase separation. Using the triple cycloaddition of ynolates with benzynes, we prepared amphiphilic triptycene derivatives bearing hydrophobic alkyl chains and hydrophilic headgroups. Among them, trialkyl-substituted triptycene (lipid mimic C) induces phase separation and thus, C-rich domain formation in dimyristoylphosphatidylcholine (DMPC) bilayers. X-ray diffraction analysis revealed that the C-rich domains consist of 2:1 DMPC:C and preserve gel-phase-like lipid packing at 30 \u00b0C. Moreover, the C-rich domains exhibit exceptional thermal stability because the C-rich\/C-poor phase separation persists up to 58 \u00b0C. Calorimetry and fluorescence observations indicated that DMPC\/C bilayers undergo fluid\/fluid phase separation, which is rare phenomena in binary lipid mixtures, around 50 \u00b0C. Monolayer measurements suggested the embedding of triptycene units and lipid molecules into the interblade spaces of the triptycene. These results indicate that domain stabilization arises from a dual embedding mechanism: interdigitation between neighboring triptycene frameworks and the cooperative incorporation of surrounding lipid molecules into the grooves of triptycene. This study established a design principle for thermally stable artificial membrane domains and provided a platform for compartmentalized membrane materials that can exploit the clustering effects of functional molecules.<\/jats:p>","DOI":"10.1021\/jacs.6c05364","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T14:02:53Z","timestamp":1785852173000},"page":"33118-33128","source":"Crossref","is-referenced-by-count":0,"title":["Triptycene-Based Lipid\nMimics for Thermally Stable\nMembrane Phase Separation"],"prefix":"10.1021","volume":"148","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8991-9248","authenticated-orcid":true,"given":"Takayuki","family":"Iwata","sequence":"first","affiliation":[{"name":"Kyushu University , , 6-1 Kasugako-en , , ,","place":["Kasuga, Fukuoka, Japan, 816-8580"]},{"name":"The University of Osaka , , 1-1 Machikaneyama , , ,","place":["Toyonaka, Osaka, Japan, 560-0043"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8868-431X","authenticated-orcid":true,"given":"Masanao","family":"Kinoshita","sequence":"additional","affiliation":[{"name":"Gunma University , , 4-2 Aramaki , , ,","place":["Maebashi, Gunma, Japan, 371\u22128510"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Itsuki","family":"Higashionna","sequence":"additional","affiliation":[{"name":"Kyushu University , , 6-1 Kasugako-en , , ,","place":["Kasuga, Fukuoka, Japan, 816-8580"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0495-2044","authenticated-orcid":true,"given":"Nobuaki","family":"Matsumori","sequence":"additional","affiliation":[{"name":"Kyushu University , , 744 Motooka , , ,","place":["Nishi-ku, Fukuoka, Japan, 819-0395"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0588-8075","authenticated-orcid":true,"given":"Mitsuru","family":"Shindo","sequence":"additional","affiliation":[{"name":"Kyushu University , , 6-1 Kasugako-en , , ,","place":["Kasuga, Fukuoka, Japan, 816-8580"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,31]]},"reference":[{"key":"2026081210080164200_cit1","doi-asserted-by":"publisher","first-page":"107","DOI":"10.1038\/s41580-022-00524-4","article-title":"Regulation of membrane protein structure and function by their lipid\nnano-environment","volume":"24","author":"Levental","year":"2023","journal-title":"Nat. Rev. Mol. Cell Biol."},{"key":"2026081210080164200_cit2","doi-asserted-by":"publisher","first-page":"750","DOI":"10.1038\/s41589-023-01268-8","article-title":"Membrane\nphase separation drives responsive assembly of receptor signaling\ndomains","volume":"19","author":"Shelby","year":"2023","journal-title":"Nat. Chem. Biol."},{"key":"2026081210080164200_cit3","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1091\/mbc.E20-12-0809","article-title":"Cholesterol- and actin-centered view\nof the plasma membrane: updating the Singer\u2013Nicolson fluid\nmosaic model to commemorate its 50th anniversary","volume":"34","author":"Kusumi","year":"2023","journal-title":"Mol. Biol. Cell"},{"key":"2026081210080164200_cit4","doi-asserted-by":"publisher","first-page":"1183","DOI":"10.1083\/jcb.201607086","article-title":"Raft-based\nsphingomyelin interactions revealed by new fluorescent sphingomyelin\nanalogs","volume":"216","author":"Kinoshita","year":"2017","journal-title":"J. Cell Biol."},{"key":"2026081210080164200_cit5","doi-asserted-by":"publisher","first-page":"4558","DOI":"10.1073\/pnas.1418088112","article-title":"Sphingomyelin\ndistribution in lipid rafts of artificial monolayer membranes visualized\nby Raman microscopy","volume":"112","author":"Ando","year":"2015","journal-title":"Proc. Natl. Acad. Sci.\nU. S. A."},{"key":"2026081210080164200_cit6","doi-asserted-by":"publisher","first-page":"46","DOI":"10.1126\/science.1174621","article-title":"Lipid Rafts as a Membrane-Organizing Principle","volume":"327","author":"Lingwood","year":"2010","journal-title":"Science"},{"key":"2026081210080164200_cit7","doi-asserted-by":"publisher","first-page":"387","DOI":"10.1007\/s12195-017-0489-4","article-title":"Phase-Separated\nLiposomes Enhance the Efficiency of Macromolecular Delivery to the\nCellular Cytoplasm","volume":"10","author":"Imam","year":"2017","journal-title":"Cell. Mol. Bioeng."},{"key":"2026081210080164200_cit8","doi-asserted-by":"publisher","first-page":"2627","DOI":"10.1021\/acs.nanolett.1c04365","article-title":"Lipid Phase\nSeparation in Vesicles Enhances TRAIL-Mediated Cytotoxicity","volume":"22","author":"Vu","year":"2022","journal-title":"Nano Lett."},{"key":"2026081210080164200_cit9","doi-asserted-by":"publisher","first-page":"1574","DOI":"10.1021\/acs.biomac.2c01338","article-title":"Tuning Targeted\nLiposome Avidity\nto Cells via Lipid Phase Separation","volume":"24","author":"Vu","year":"2023","journal-title":"Biomacromolecules"},{"key":"2026081210080164200_cit10","doi-asserted-by":"publisher","first-page":"402","DOI":"10.1039\/D3NA00841J","article-title":"Tuning of TRAIL\nClustering on the Surface of Nanoscale\nLiposomes by Phase Separation","volume":"6","author":"Zhang","year":"2024","journal-title":"Nanoscale Adv."},{"key":"2026081210080164200_cit11","doi-asserted-by":"publisher","first-page":"630","DOI":"10.1016\/j.chemphyslip.2012.06.006","article-title":"Effect of\ntemperature on the formation\nof liquid phase-separating giant unilamellar vesicles (GUV)","volume":"165","author":"Betaneli","year":"2012","journal-title":"Chem. Phys. Lipids"},{"key":"2026081210080164200_cit12","doi-asserted-by":"publisher","first-page":"184036","DOI":"10.1016\/j.bbamem.2022.184036","article-title":"Impact of sphingomyelin acyl chain\nheterogeneity upon properties of raft-like membranes","volume":"1864","author":"Hirano","year":"2022","journal-title":"Biochim. Biophys. Acta - Biomembr."},{"key":"2026081210080164200_cit13","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202414847","article-title":"Selective\nGlycan Presentation\nin Liquid-Ordered or -Disordered Membrane Phases and its Effect on\nLectin Binding","volume":"64","author":"Blawitzki","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210080164200_cit14","doi-asserted-by":"publisher","first-page":"207","DOI":"10.1146\/annurev.biophys.093008.131238","article-title":"Phase separation\nin biolog","volume":"39","author":"Elson","year":"2010","journal-title":"Annu.\nRev. 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Rev."},{"key":"2026081210080164200_cit17","doi-asserted-by":"publisher","first-page":"97","DOI":"10.1016\/j.bbamem.2008.08.022","article-title":"Ordering Effects\nof Cholesterol and Its Analogues","volume":"1788","author":"Ro\u0301g","year":"2009","journal-title":"Biochim. Biophys.\nActa Biomembr."},{"key":"2026081210080164200_cit18","doi-asserted-by":"publisher","first-page":"4094","DOI":"10.1021\/ja974379+","article-title":"Supramolecular Membranes.\nSpontaneous Assembly of Aqueous\nBilayer Membrane via Formation of Hydrogen Bonded Pairs of Melamine\nand Cyanuric Acid Derivatives","volume":"120","author":"Kimizuka","year":"1998","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026081210080164200_cit19","doi-asserted-by":"publisher","first-page":"14456","DOI":"10.1021\/ja806954u","article-title":"Intra- and\nIntermembrane Pairwise Molecular Recognition between Synthetic Hydrogen-Bonding\nPhospholipids","volume":"130","author":"Ma","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"2026081210080164200_cit20","doi-asserted-by":"publisher","first-page":"8840","DOI":"10.1002\/chem.201405994","article-title":"Dendritic Domains with Hexagonal\nSymmetry Formed by X-Shaped Bolapolyphiles in Lipid Membranes","volume":"21","author":"Werner","year":"2015","journal-title":"Chem.\u2500Eur. J."},{"key":"2026081210080164200_cit21","doi-asserted-by":"publisher","first-page":"673","DOI":"10.1021\/acs.langmuir.5b03712","article-title":"Self-Assembly\nof X-Shaped Bolapolyphiles in Lipid Membranes: Solid-State NMR Investigations","volume":"32","author":"Achilles","year":"2016","journal-title":"Langmuir"},{"key":"2026081210080164200_cit22","doi-asserted-by":"publisher","first-page":"4106","DOI":"10.1039\/D1CC01111A","article-title":"Calcium-induced\nreversible assembly of phosphorylated amphiphile within lipid bilayer\nmembranes","volume":"57","author":"Shimizu","year":"2021","journal-title":"Chem. Commun."},{"key":"2026081210080164200_cit23","doi-asserted-by":"publisher","first-page":"1139","DOI":"10.1002\/anie.201408101","article-title":"Sequential\nSynthesis of Coordination Polymersomes","volume":"54","author":"Ohtani","year":"2015","journal-title":"Angew.\nChem., Int. Ed."},{"key":"2026081210080164200_cit24","doi-asserted-by":"publisher","first-page":"17931","DOI":"10.1002\/anie.202006600","article-title":"Pseudo-Membrane Jackets: Two-Dimensional Coordination\nPolymers Achieving Visible Phase Separation in Cell Membrane A representative\nexample","volume":"59","author":"Ohtani","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210080164200_cit25","doi-asserted-by":"publisher","first-page":"13603","DOI":"10.1002\/anie.202102774","article-title":"Metal Complex Lipids\nfor Fluid\u2013Fluid\nPhase Separation in Coassembled Phospholipid Membranes","volume":"60","author":"Ohtani","year":"2021","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210080164200_cit26","volume-title":"Iptycenes Chemistry From Synthesis\nto Applications","author":"Chen","year":"2012"},{"key":"2026081210080164200_cit27","doi-asserted-by":"publisher","first-page":"10047","DOI":"10.1039\/D1OB01818C","article-title":"Recent advances\non triptycene derivatives in supramolecular\nand materials chemistry","volume":"19","author":"Gu","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"2026081210080164200_cit28","doi-asserted-by":"publisher","first-page":"1181","DOI":"10.1021\/ar800107v","article-title":"Iptycenes in the\nDesign of High Performance\nPolymers","volume":"41","author":"Swager","year":"2008","journal-title":"Acc. Chem. Res."},{"key":"2026081210080164200_cit29","doi-asserted-by":"publisher","first-page":"1398","DOI":"10.1039\/c39900001398","article-title":"Epitaxygens: Mesophases\nbased on the Triptycene Molecular Subunit","author":"Norvez","year":"1990","journal-title":"J.\nChem. Soc., Chem. Commun."},{"key":"2026081210080164200_cit30","doi-asserted-by":"publisher","first-page":"1389","DOI":"10.1080\/02678299308026451","article-title":"Epitaxygens: mesomorphic properties of triptycene derivatives","volume":"14","author":"Norvez","year":"1993","journal-title":"Liq. Cryst."},{"key":"2026081210080164200_cit31","doi-asserted-by":"publisher","first-page":"2414","DOI":"10.1021\/jo00061a012","article-title":"Liquid Crystalline\nTriptycene Derivatives","volume":"58","author":"Norvez","year":"1993","journal-title":"J. Org. Chem."},{"key":"2026081210080164200_cit32","doi-asserted-by":"publisher","first-page":"1122","DOI":"10.1126\/science.aab1391","article-title":"Rational synthesis\nof organic thinfilms with exceptional long-rangestructural integrity","volume":"348","author":"Seiki","year":"2015","journal-title":"Science"},{"key":"2026081210080164200_cit33","doi-asserted-by":"publisher","first-page":"1298","DOI":"10.1002\/anie.201609111","article-title":"Regioselective One-Pot\nSynthesis of Triptycenes via Triple-Cycloadditions of Arynes to Ynolates","volume":"56","author":"Umezu","year":"2017","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210080164200_cit34","doi-asserted-by":"publisher","first-page":"13855","DOI":"10.1002\/chem.201903024","article-title":"Synthesis of Distorted\n1,8,13-Trisilyl-9-hydroxytriptycenes by Triple Cycloaddition of Ynolates\nto 3-Silylbenzynes","volume":"25","author":"Yoshinaga","year":"2019","journal-title":"Chem.\u2500Eur. J."},{"key":"2026081210080164200_cit35","doi-asserted-by":"publisher","first-page":"1084","DOI":"10.1246\/cl.200412","article-title":"Synthesis\nof 9-Hydroxytriptycenes\nBearing a Functionalized Substituent at the C-10 Position through\na Triple Cycloaddition Reaction of Ynolates Derived from 2,6-Di-tert-butylphenyl Esters","volume":"49","author":"Sun","year":"2020","journal-title":"Chem. Lett."},{"key":"2026081210080164200_cit36","doi-asserted-by":"publisher","first-page":"1903","DOI":"10.1055\/s-0040-1706417","article-title":"Flow Synthesis of Triptycene via\nTriple Cycloaddition of Ynolate to Benzyne","volume":"31","author":"Iwata","year":"2020","journal-title":"Synlett"},{"key":"2026081210080164200_cit37","doi-asserted-by":"publisher","first-page":"4971","DOI":"10.1055\/a-1818-0576","article-title":"3-Trifluoromethylbenzyne: Precise\nOrientation in Cycloaddition Reaction Enabled Regioselective Synthesis\nof Trifluoromethylated Triptycenes","volume":"54","author":"Iwata","year":"2022","journal-title":"Synthesis"},{"key":"2026081210080164200_cit38","doi-asserted-by":"publisher","first-page":"7852","DOI":"10.1021\/acs.orglett.5c02031","article-title":"One-Pot Synthesis of\nIptycenes and Dissymmetric Triptycenes Using Ynolate-Benzyne Triple\nCycloaddition","volume":"27","author":"Iwata","year":"2025","journal-title":"Org. Lett."},{"key":"2026081210080164200_cit39","doi-asserted-by":"publisher","first-page":"39","DOI":"10.1246\/cl.200600","article-title":"Synthesis of 1,8,13-Substituted\nTriptycenes","volume":"50","author":"Iwata","year":"2021","journal-title":"Chem. Lett."},{"key":"2026081210080164200_cit40","doi-asserted-by":"publisher","first-page":"17160","DOI":"10.1021\/ja052939w","article-title":"Prevention of Undesirable\nIsomerization during Olefin Metathesis","volume":"127","author":"Hong","year":"2005","journal-title":"J. Am.\nChem. Soc."},{"key":"2026081210080164200_cit41","doi-asserted-by":"publisher","first-page":"3936","DOI":"10.1021\/jo00332a045","article-title":"A greatly\nimproved procedure for ruthenium tetroxide catalyzed oxidations of\norganic compounds","volume":"46","author":"Carlsen","year":"1981","journal-title":"J. Org. Chem."},{"key":"2026081210080164200_cit42","doi-asserted-by":"publisher","first-page":"75","DOI":"10.1016\/j.cocis.2007.05.005","article-title":"Fatty Acid Vesicles","volume":"12","author":"Morigaki","year":"2007","journal-title":"Curr. Opin. Colloid Interface Sci."},{"key":"2026081210080164200_cit43","doi-asserted-by":"publisher","first-page":"1407","DOI":"10.1007\/s10973-016-5408-8","article-title":"DSC and Raman\nstudy of DMPC liposomes in presence of Ibuprofen at different pH","volume":"127","author":"Di Foggia","year":"2017","journal-title":"J. Therm. Anal. Calorim."},{"key":"2026081210080164200_cit44","doi-asserted-by":"publisher","first-page":"847","DOI":"10.1021\/bi00881a008","article-title":"Interaction of Organic\nMercurial Compounds with Dihydrofolate\nReductase from Ehrlich Ascites Carcinoma Cells","volume":"4","author":"Perkins","year":"1965","journal-title":"Biochemistry"},{"key":"2026081210080164200_cit45","doi-asserted-by":"publisher","first-page":"1372","DOI":"10.1016\/j.bbamem.2014.01.017","article-title":"Coexistence of two liquid crystalline\nphases in dihydrosphingomyelin and dioleoylphosphatidylcholine binary\nmixtures","volume":"1838","author":"Kinoshita","year":"2014","journal-title":"Biochim. Biophys. Acta"},{"key":"2026081210080164200_cit46","doi-asserted-by":"publisher","first-page":"2459","DOI":"10.1016\/S0006-3495(00)76790-7","article-title":"Dimyristoylphosphatidylcholine\/C16:0-ceramide\nbinary liposomes studied by differential scanning calorimetry and\nwide- and small-angle x-ray scattering","volume":"78","author":"Holopainen","year":"2000","journal-title":"Biophys.\nJ."},{"key":"2026081210080164200_cit47","doi-asserted-by":"publisher","first-page":"104835","DOI":"10.1016\/j.chemphyslip.2019.104835","article-title":"The influence of ceramide and its\ndihydro analog on the physico-chemical properties of sphingomyelin\nbilayers","volume":"226","author":"Kinoshita","year":"2020","journal-title":"Chem. Phys. Lipids"},{"key":"2026081210080164200_cit48","doi-asserted-by":"publisher","first-page":"1881","DOI":"10.1139\/v60-253","article-title":"Relaxation of Surface Pressure and\nCollapse of Steric Acid","volume":"38","author":"Rabinovitch","year":"1960","journal-title":"Can. J. Chem."},{"key":"2026081210080164200_cit49","doi-asserted-by":"publisher","first-page":"301","DOI":"10.1016\/0005-2736(68)90115-6","article-title":"Monolayer characteristics\nof saturated 1,2-diacyl phosphatidylcholines\n(lecithins) and phosphatidylethanolamines at the air-water interface","volume":"163","author":"Phillips","year":"1968","journal-title":"Biochim. Biophys. Acta"},{"key":"2026081210080164200_cit50","doi-asserted-by":"publisher","first-page":"97","DOI":"10.1016\/0005-2736(75)90045-0","article-title":"Relation between various phospholipase actions on human\nred cell membranes and the interfacial phospholipid pressure in monolayers","volume":"406","author":"Demel","year":"1975","journal-title":"Biochim. Biophys. 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