{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,17]],"date-time":"2026-03-17T03:53:18Z","timestamp":1773719598551,"version":"3.50.1"},"reference-count":50,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2019,4,17]],"date-time":"2019-04-17T00:00:00Z","timestamp":1555459200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Visible-light-driven photocatalytic supramolecular enantiodifferentiating dimerization of 2-anthracenecarboxylic acid (AC) through triplet-triplet annihilation (TTA), mediated by the Schiff base Pt(II) complex (Pt-1, Pt-2, and Pt-3) was studied. The host concentration and the temperature effects on the stereoselectivity were comprehensively investigated. Increasing the concentration of sensitizers\/hosts significantly enhanced the conversion of the photoreaction but led to reduced enantioselectivities of the chiral photodimers 2 and 3 when the photoreaction was triggered by a 532 nm laser, which was in contrast with the results obtained by direct irradiation of AC with a 365 nm light-emitting diode (LED) lamp, due to the aggregation of the sensitizer\/host in water. The cyclization of AC through triplet-triplet annihilation displayed significant temperature dependency when Pt-3 was employed as the sensitizer\/host. Increasing the temperature from 0 \u00b0C to 30 \u00b0C with 5% equiv. of Pt-3 led to a great increase of the ee of 2 from 2.1% to 31.6%. However, hardly any temperature dependency was observed when the photodimerization was mediated by other sensitizers and\/or hosts, or the photoreaction was triggered directly with a 365 nm LED lamp.<\/jats:p>","DOI":"10.3390\/molecules24081502","type":"journal-article","created":{"date-parts":[[2019,4,17]],"date-time":"2019-04-17T07:58:09Z","timestamp":1555487889000},"page":"1502","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Effects of Temperature and Host Concentration on the Supramolecular Enantiodifferentiating [4 + 4] Photodimerization of 2-Anthracenecarboxylate through Triplet-Triplet Annihilation Catalyzed by Pt-Modified Cyclodextrins"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6271-7248","authenticated-orcid":false,"given":"Ming","family":"Rao","sequence":"first","affiliation":[{"name":"Key Laboratory of Green Chemistry &amp; Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, 29 Wangjiang Road, Chengdu 610064, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8969-1148","authenticated-orcid":false,"given":"Wanhua","family":"Wu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Chemistry &amp; Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, 29 Wangjiang Road, Chengdu 610064, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2049-1324","authenticated-orcid":false,"given":"Cheng","family":"Yang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Chemistry &amp; Technology, College of Chemistry, and Healthy Food Evaluation Research Center, Sichuan University, 29 Wangjiang Road, Chengdu 610064, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,4,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1038\/nature13892","article-title":"Asymmetric photoredox transition-metal catalysis activated by visible light","volume":"515","author":"Huo","year":"2014","journal-title":"Nature"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"5338","DOI":"10.1021\/ja050704e","article-title":"Electrostatic manipulation of enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate within \u03b3-cyclodextrin cavity through chemical modification. inverted product distribution and enhanced enantioselectivity","volume":"127","author":"Nakamura","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3126","DOI":"10.1021\/jo0601718","article-title":"Pressure and temperature-controlled enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylate mediated by secondary face- and skeleton-modified \u03b3-cyclodextrins","volume":"71","author":"Yang","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3005","DOI":"10.1021\/ol061004x","article-title":"Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by \u03b3-cyclodextrins with a flexible or rigid cap","volume":"8","author":"Yang","year":"2006","journal-title":"Org. Lett."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"5786","DOI":"10.1021\/jo800533y","article-title":"Supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by capped \u03b3-cyclodextrins: Critical control of enantioselectivity by cap rigidity","volume":"73","author":"Yang","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"8574","DOI":"10.1021\/ja8032923","article-title":"Highly stereoselective photocyclodimerization of \u03b3-cyclodextrin-appended anthracene mediated by \u03b3-cyclodextrin and cucurbit[8]uril: A dramatic steric effect operating outside the binding site","volume":"130","author":"Yang","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"290","DOI":"10.3762\/bjoc.7.38","article-title":"Supramolecular FRET photocyclodimerization of anthracenecarboxylate with naphthalene-capped \u03b3-cyclodextrin","volume":"7","author":"Wang","year":"2011","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"6849","DOI":"10.1039\/c1cc11771h","article-title":"Wavelength-controlled supramolecular photocyclodimerization of anthracenecarboxylate mediated by \u03b3-cyclodextrins","volume":"47","author":"Wang","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"13786","DOI":"10.1021\/ja202020x","article-title":"Dual supramolecular photochirogenesis: Ultimate stereocontrol of photocyclodimerization by a chiral scaffold and confining host","volume":"133","author":"Yang","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"6916","DOI":"10.1021\/ja5032908","article-title":"Ammonia-driven chirality inversion and enhancement in enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate mediated by diguanidino-\u03b3-cyclodextrin","volume":"136","author":"Yao","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/j.cclet.2017.05.004","article-title":"Switched enantioselectivity by solvent components and temperature in photocyclodimerization of 2-anthracenecarboxylate with 6 A,6 X-diguanidio-\u03b3-cyclodextrins","volume":"29","author":"Yi","year":"2018","journal-title":"Chin. Chem. Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1071\/CH08143","article-title":"pH-Controlled supramolecular enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate with capped \u03b3-cyclodextrins","volume":"61","author":"Yang","year":"2008","journal-title":"Aust. J. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"190","DOI":"10.1039\/c3pp50255d","article-title":"Manipulating \u03b3-cyclodextrin-mediated photocyclodimerization of anthracenecarboxylate by wavelength, temperature, solvent and host","volume":"13","author":"Yang","year":"2014","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3430","DOI":"10.1021\/acs.joc.6b00130","article-title":"Inherently chiral azonia[6]helicene-modified \u03b2-cyclodextrin: Synthesis, characterization, and chirality sensing of underivatized amino acids in water","volume":"81","author":"Huang","year":"2016","journal-title":"J. Org. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Liu, R., Zhang, Y., Liang, W., Wu, W., Huang, Q., Yu, X., Xu, W., Zhou, D., and Yang, C. (2018). Temperature-driven braking of \u03b3-cyclodextrin-curcubit[6]uril-cowheeled[4]rotaxanes. Chin. Chem. Lett.","DOI":"10.1016\/j.cclet.2018.12.002"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3073","DOI":"10.1021\/jo302818w","article-title":"Cross- versus homo-photocyclodimerization of anthracene and 2-anthracenecarboxylic acid mediated by a chiral hydrogen-bonding template. Factors controlling the cross-\/homo-selectivity and enantioselectivity","volume":"78","author":"Kawanami","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"7908","DOI":"10.1021\/jo901792t","article-title":"Supramolecular complexation and enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid with 4-aminoprolinol derivatives as chiral hydrogen-bonding templates","volume":"74","author":"Kawanami","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"12187","DOI":"10.1021\/jacs.6b05598","article-title":"Supramolecular photochirogenesis with a higher-order complex: Highly accelerated exclusively head-to-head photocyclodimerization of 2-anthracenecarboxylic acid via 2:2 complexation with prolinol","volume":"138","author":"Kawanami","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1139","DOI":"10.1038\/nature03955","article-title":"Catalytic enantioselective reactions driven by photoinduced electron transfer","volume":"436","author":"Bauer","year":"2005","journal-title":"Nature"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1017","DOI":"10.1016\/j.cclet.2016.04.021","article-title":"Enhanced head-to-head photodimers in the photocyclodimerization of anthracenecarboxylic acid with a cationic pillar[6]arene","volume":"27","author":"Gui","year":"2016","journal-title":"Chin. Chem. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1016\/j.jphotochem.2015.10.023","article-title":"Enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylate mediated by a self-assembled iron tetrahedral coordination cage","volume":"331","author":"Alagesan","year":"2016","journal-title":"J. Photochem. Photobiol. A: Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"7492","DOI":"10.1021\/ja034641g","article-title":"Bovine serum albumin-mediated enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate","volume":"125","author":"Wada","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3478","DOI":"10.1021\/ja068475z","article-title":"Supramolecular photochirogenesis with biomolecules. Mechanistic studies on the enantiodifferentiation for the photocyclodimerization of 2-anthracenecarboxylate mediated by bovine serum albumin","volume":"129","author":"Nishijima","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"4123","DOI":"10.1039\/C3CS60339C","article-title":"Supramolecular photochirogenesis","volume":"43","author":"Yang","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3872","DOI":"10.1002\/anie.201411409","article-title":"Enantioselective catalysis of photochemical reactions","volume":"54","author":"Richard","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_26","first-page":"9","article-title":"Catalytic supramolecular photochirogenesis","volume":"2","author":"Yan","year":"2015","journal-title":"Supramol. Catal."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"6675","DOI":"10.1002\/anie.200902911","article-title":"Catalytic enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by a non-sensitizing chiral metallosupramolecular host","volume":"48","author":"Ke","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"840","DOI":"10.1126\/science.1244809","article-title":"Enantioselective Lewis acid catalysis of intramolecular enone [2+2] photocycloaddition reactions","volume":"342","author":"Brimioulle","year":"2013","journal-title":"Science"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1680","DOI":"10.1021\/acs.orglett.8b00520","article-title":"Photocatalytic supramolecular enantiodifferentiating dimerization of 2-anthracenecarboxylic acid through triplet-triplet annihilation","volume":"20","author":"Rao","year":"2018","journal-title":"Org. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"937","DOI":"10.1039\/c1ra00469g","article-title":"Triplet\u2013triplet annihilation based upconversion: From triplet sensitizers and triplet acceptors to upconversion quantum yields","volume":"1","author":"Zhao","year":"2011","journal-title":"RSC Adv."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2560","DOI":"10.1016\/j.ccr.2010.01.003","article-title":"Photon upconversion based on sensitized triplet\u2013triplet annihilation","volume":"254","author":"Singhrachford","year":"2010","journal-title":"Coordin. Chem. Rev. 3. Photochem. Photobid. A: Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"12652","DOI":"10.1021\/ja075014k","article-title":"Noncoherent low-power upconversion in solid polymer films","volume":"129","author":"Islangulov","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"3327","DOI":"10.1016\/j.solmat.2005.09.021","article-title":"Efficiency enhancement of solar cells by luminescent up-conversion of sunlight","volume":"90","author":"Trupke","year":"2006","journal-title":"Sol. Ene. Mater. Solar Cells"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"17478","DOI":"10.1021\/ja308789u","article-title":"Encapsulated triplet-triplet annihilation-based upconversion in the aqueous phase for sub-band-gap semiconductor photocatalysis","volume":"134","author":"Kim","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"8447","DOI":"10.1002\/adfm.201603303","article-title":"Self-assembled dual dye-doped nanosized micelles for high-contrast up-conversion bioimaging","volume":"26","author":"Mattiello","year":"2016","journal-title":"Adv. Func. Mater."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"155122","DOI":"10.1103\/PhysRevB.77.155122","article-title":"Upconversion-induced delayed fluorescence in multicomponent organic systems: Role of Dexter energy transfer","volume":"77","author":"Monguzzi","year":"2008","journal-title":"Physical Review B"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"15405","DOI":"10.1021\/jacs.6b07946","article-title":"Enhanced triplet-triplet energy transfer and upconversion fluorescence through host-guest complexation","volume":"138","author":"Fan","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3147","DOI":"10.1002\/1521-3773(20020902)41:17<3147::AID-ANIE3147>3.0.CO;2-V","article-title":"Asymmetric photochemistry and photochirogenesis","volume":"17","author":"Griesbeck","year":"2002","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Inoue, Y., and Ramamurthy, V. (2004). Chiral Photochemistry, Marcel Dekker.","DOI":"10.1201\/9780203026342"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Ramamurthy, V., and Inoue, Y. (2011). Supramolecular Photochemistry, Wiley.","DOI":"10.1002\/9781118095300"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4084","DOI":"10.1039\/c3cs60471c","article-title":"Supramolecular photocatalysis: Combining confinement and non-covalent interactions to control light initiated reactions","volume":"43","author":"Vallavoju","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"4990","DOI":"10.1021\/ja300522y","article-title":"Theoretical and experimental investigations of circular dichroism and absolute configuration determination of chiral anthracene photodimers","volume":"134","author":"Wakai","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"966","DOI":"10.1021\/ja016238k","article-title":"Supramolecular catalysis of the enantiodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylate by \u03b3-cyclodextrin","volume":"125","author":"Nakamura","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"374","DOI":"10.1016\/j.jphotochem.2018.11.038","article-title":"Enhanced irregular photodimers and switched enantioselectivity by solvent and temperature in the photocyclodimerization of 2-anthracenecarboxylate with modified \u03b2-cyclodextrins","volume":"371","author":"Wei","year":"2019","journal-title":"J. Photochem. Photobio. A: Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"3959","DOI":"10.1021\/jacs.7b12085","article-title":"Supramolecular photochirogenesis driven by higher-order complexation: Enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate to slipped cyclodimers via a 2:2 complex with \u03b2-cyclodextrin","volume":"140","author":"Wei","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"39","DOI":"10.2174\/138527211793797837","article-title":"The use of calixarenes in asymmetric catalysis","volume":"15","author":"Li","year":"2011","journal-title":"Curr. Org. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"16677","DOI":"10.1002\/chem.201804001","article-title":"Supramolecular Assembly-Improved Triplet-Triplet Annihilation Upconversion in Aqueous Solution","volume":"24","author":"Xu","year":"2018","journal-title":"Chem. Eur. J."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1007\/BF00662250","article-title":"Acceleration of the photodimerization of water-soluble anthracenes included by \u03b2- and \u03b3-cyclodextrins","volume":"2","author":"Tamaki","year":"1984","journal-title":"J. Incl. Phenom."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"11550","DOI":"10.1039\/c1dt11001b","article-title":"Tuning the emissive triplet excited states of platinum(II) Schiff base complexes with pyrene, and application for luminescent oxygen sensing and triplet-triplet-annihilation based upconversions","volume":"40","author":"Wu","year":"2011","journal-title":"Dalton Trans"},{"key":"ref_50","first-page":"327","article-title":"A simple rule for predicting circular-dichroism induced in aromatic guests by cyclodextrin hosts in inclusion complexes","volume":"110","author":"Kuthi","year":"1982","journal-title":"Chim.Acad. Sci. Hung"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/8\/1502\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T12:46:01Z","timestamp":1760186761000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/8\/1502"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,4,17]]},"references-count":50,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2019,4]]}},"alternative-id":["molecules24081502"],"URL":"https:\/\/doi.org\/10.3390\/molecules24081502","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,4,17]]}}}