{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T10:45:58Z","timestamp":1790937958419,"version":"4.1.0"},"reference-count":35,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2012,4,12]],"date-time":"2012-04-12T00:00:00Z","timestamp":1334188800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Photochem &amp; Photobiology"],"published-print":{"date-parts":[[2012,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>ArgenCast\u20101 (<jats:bold>1<\/jats:bold>), a photocage for silver utilizing acyclic polythioether 3,6,12,15\u2010tetrathia\u20109\u2010azaheptadecane receptor and 4,5\u2010dimethoxy\u20102\u2010nitrobenzyl (DMNB) chromophore has been prepared using trimethylsilyl trifluoromethanesulfonate\u2010assisted electrophilic aromatic substitution. Metal binding studies with ArgenCast\u20101 reveal interactions with Ag<jats:sup>+<\/jats:sup>, Hg<jats:sup>2+<\/jats:sup> and Cu<jats:sup>+<\/jats:sup>, but only Ag<jats:sup>+<\/jats:sup> coordinates in both aqueous and organic solvents. The uncaging mechanism of ArgenCast\u20101 metal complex involves a photoreaction that converts the nitrobenzydrol into the electron withdrawing nitrosobenzophenone that participates in a resonance interaction with a metal\u2010bound aniline nitrogen atom. The structural change following photolysis decreases availability of the nitrogen lone pair for Ag<jats:sup>+<\/jats:sup> coordination, but strong interactions between Ag<jats:sup>+<\/jats:sup> and the thioether ligands mitigates metal ion release. A resonance interaction with a key <jats:bold><jats:italic>aci<\/jats:italic><\/jats:bold>\u2010nitro intermediate reduces the photolysis quantum yield of ArgenCast\u20101, so several naphthyl\u2010based nitrobenzyl groups were screened as alternatives to DMNB. The naphthyl Ag<jats:sup>+<\/jats:sup> photocages, ArgenCast\u20102 and \u20103, exhibit nearly identical quantum yield to ArgenCast\u20101 owing to the dominance of resonance between <jats:italic>aci<\/jats:italic>\u2010nitro intermediate and the aniline nitrogen atom.<\/jats:p>","DOI":"10.1111\/j.1751-1097.2012.01136.x","type":"journal-article","created":{"date-parts":[[2012,3,8]],"date-time":"2012-03-08T19:37:22Z","timestamp":1331235442000},"page":"844-850","source":"Crossref","is-referenced-by-count":8,"title":["Understanding the Relationship Between Photolysis Efficiency and Metal Binding Using ArgenCast Photocages"],"prefix":"10.1111","volume":"88","author":[{"given":"Hannah W.","family":"Mbatia","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel P.","family":"Kennedy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shawn C.","family":"Burdette","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2012,4,12]]},"reference":[{"key":"e_1_2_5_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00603a020"},{"key":"e_1_2_5_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cb900036s"},{"key":"e_1_2_5_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-3495(86)83525-1"},{"key":"e_1_2_5_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol900902z"},{"key":"e_1_2_5_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic901182c"},{"key":"e_1_2_5_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol101726a"},{"key":"e_1_2_5_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201000673"},{"key":"e_1_2_5_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/b913605c"},{"key":"e_1_2_5_10_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1471-4159.2011.07417.x"},{"key":"e_1_2_5_11_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10534-005-4451-x"},{"key":"e_1_2_5_12_2","doi-asserted-by":"publisher","DOI":"10.1093\/jac\/dkh478"},{"key":"e_1_2_5_13_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.68.3071"},{"key":"e_1_2_5_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19800630827"},{"key":"e_1_2_5_15_2","volume-title":"XLfit, 5.1.0.0","author":"ID Business Solutions Limited","year":"2009"},{"key":"e_1_2_5_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906500m"},{"key":"e_1_2_5_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603992"},{"key":"e_1_2_5_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja055064u"},{"key":"e_1_2_5_19_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0406547102"},{"key":"e_1_2_5_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo9819584"},{"key":"e_1_2_5_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200902005"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/b908969a"},{"key":"e_1_2_5_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701785"},{"key":"e_1_2_5_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0706399"},{"key":"e_1_2_5_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja052574f"},{"key":"e_1_2_5_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol2013632"},{"key":"e_1_2_5_27_2","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2006.140"},{"key":"e_1_2_5_28_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio.69"},{"key":"e_1_2_5_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2004158"},{"key":"e_1_2_5_30_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1009932108"},{"key":"e_1_2_5_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja907778b"},{"key":"e_1_2_5_32_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmeth821"},{"key":"e_1_2_5_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol902807q"},{"key":"e_1_2_5_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/bc020021d"},{"key":"e_1_2_5_35_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.08.019"},{"key":"e_1_2_5_36_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2011.07.043"}],"container-title":["Photochemistry and Photobiology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1111%2Fj.1751-1097.2012.01136.x","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/j.1751-1097.2012.01136.x","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,14]],"date-time":"2023-10-14T20:13:18Z","timestamp":1697314398000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1111\/j.1751-1097.2012.01136.x"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,4,12]]},"references-count":35,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2012,7]]}},"alternative-id":["10.1111\/j.1751-1097.2012.01136.x"],"URL":"https:\/\/doi.org\/10.1111\/j.1751-1097.2012.01136.x","archive":["Portico"],"relation":{},"ISSN":["0031-8655","1751-1097"],"issn-type":[{"value":"0031-8655","type":"print"},{"value":"1751-1097","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,4,12]]}}}