{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,12]],"date-time":"2026-04-12T12:12:28Z","timestamp":1775995948303,"version":"3.50.1"},"reference-count":27,"publisher":"American Chemical Society (ACS)","issue":"17","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Inorg. Chem."],"published-print":{"date-parts":[[2011,9,5]]},"DOI":"10.1021\/ic200727f","type":"journal-article","created":{"date-parts":[[2011,8,5]],"date-time":"2011-08-05T15:44:33Z","timestamp":1312559073000},"page":"7916-7918","source":"Crossref","is-referenced-by-count":34,"title":["Synthesis of New Metalloporphyrin Triads: Efficient and Versatile Tripod Optical Sensor for the Detection of Amines"],"prefix":"10.1021","volume":"50","author":[{"given":"Sara M. A.","family":"Pinto","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade de Coimbra, Coimbra, Portugal"}]},{"given":"Mirtha A. O.","family":"Louren\u00e7o","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade de Coimbra, Coimbra, Portugal"}]},{"given":"M\u00e1rio J. F.","family":"Calvete","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade de Coimbra, Coimbra, Portugal"}]},{"given":"Artur R.","family":"Abreu","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade de Coimbra, Coimbra, Portugal"}]},{"given":"M\u00e1rio T. S.","family":"Rosado","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade de Coimbra, Coimbra, Portugal"}]},{"given":"Hugh D.","family":"Burrows","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade de Coimbra, Coimbra, Portugal"}]},{"given":"Mariette M.","family":"Pereira","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidade de Coimbra, Coimbra, Portugal"}]}],"member":"316","published-online":{"date-parts":[[2011,8,5]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"crossref","first-page":"4719","DOI":"10.1002\/ejoc.200900512","author":"Maes W.","year":"2009","journal-title":"Eur. J. Org. Chem."},{"key":"ref2\/cit2","doi-asserted-by":"crossref","first-page":"6047","DOI":"10.1021\/cr900186c","volume":"109","author":"Li W.-S.","year":"2009","journal-title":"Chem. Rev."},{"key":"ref3\/cit3","doi-asserted-by":"crossref","first-page":"9270","DOI":"10.1002\/chem.200901597","volume":"15","author":"Caminade A. M.","year":"2009","journal-title":"Chem.\u2014Eur. J."},{"key":"ref4\/cit4","doi-asserted-by":"crossref","first-page":"352","DOI":"10.1039\/B711745K","volume":"38","author":"Carlmark A.","year":"2009","journal-title":"Chem. Soc. Rev."},{"key":"ref5\/cit5","first-page":"87","volume":"214","author":"D\u2019Ambruso G. D.","year":"2008","journal-title":"Adv. Polym. Sci."},{"key":"ref6\/cit6","doi-asserted-by":"crossref","first-page":"5568","DOI":"10.1021\/jo980846+","volume":"63","author":"Mongin O.","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref7\/cit7","volume-title":"The Porphyrin Handbook","volume":"18","author":"Harvey P. D.","year":"2003"},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"419","DOI":"10.1142\/S1088424609000723","volume":"13","author":"Pereira A. M. V. M.","year":"2009","journal-title":"J. Porphyrin Phthalocyanines"},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"1023","DOI":"10.1021\/cm000773m","volume":"13","author":"Ambroise A.","year":"2001","journal-title":"Chem. Mater."},{"key":"ref10\/cit10","doi-asserted-by":"crossref","first-page":"2297","DOI":"10.1016\/j.ccr.2010.05.014","volume":"254","author":"Jurow M.","year":"2010","journal-title":"Coord. Chem. Rev."},{"key":"ref11\/cit11","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1126\/science.257.5066.63","volume":"257","author":"O\u2019Neil M. P.","year":"1992","journal-title":"Science"},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"4477","DOI":"10.1021\/ja100192x","volume":"132","author":"Takai A.","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1039\/a909258g","author":"Hecht S.","year":"2000","journal-title":"Chem. Commun."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"11697","DOI":"10.1021\/jp102755h","volume":"114","author":"Dunbar A. D. F.","year":"2010","journal-title":"J. Phys. Chem. B"},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"6097","DOI":"10.1021\/jo000557x","volume":"65","author":"Mizutani T.","year":"2000","journal-title":"J. Org. Chem."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"22","DOI":"10.1016\/j.chroma.2007.01.114","volume":"1155","author":"DeBorba B. M.","year":"2007","journal-title":"J. Chromatogr. A"},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1897\/03-109","volume":"23","author":"Gong W.-L.","year":"2004","journal-title":"Environ. Toxicol. Chem."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1016\/S0308-8146(02)00552-6","volume":"82","author":"Shakila R. J.","year":"2003","journal-title":"Food Chem."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"635","DOI":"10.1002\/jhet.5570280317","volume":"28","author":"Gonsalves A. M. A. R.","year":"1991","journal-title":"J. Heterocycl. Chem."},{"key":"ref21\/cit21a","unstructured":"Synthesis of the Triad 1,3-bis[5-(3-hydroxyphenyl)-10,15,20-triphenylporphyrin]-2-[5-(3-hydroxyphenyl)-10,15,20-triphenylporphyrin]-2-methylpropane (3): 5-(3-Hydroxyphenyl)-10,15,20-triphenylporphyrin (0.100 g, 0.158 mmol, 1 equiv) and Cs2CO3(0.3 g, 0.948 mmol, 6 equiv) were dissolved in 2 mL of DMF. The mixture was stirred for 0.5 h at room temperature, and then2(0.02 g, 0.036 mmol,1\/4equiv) was added dropwise. The mixture was then allowed to stand for 48 h at room temperature. The crude material was extracted with CH2Cl2\/H2O (five times), and the organic phase was dried with sodium sulfate and evaporated. For purification, silica gel column chromatography was used with CH2Cl2as the eluent. The trimer was recrystallized from CH2Cl2\/n-hexane (42 mg, 42%). HRMS (ESI-TOF):m\/zcalcd978.3864,m\/zfound979.3937 ([M]2+).1H NMR (300 MHz, CDCl3): \u03b4 8.82\u20138.69 (m, 24H, \u03b2-H), 8.23\u20138.02 (m, 18H,o-H, 10,15,20-Ph), 7.83 (s, 3H,o-H, 5-Ph), 7.77\u20137.52 (m, 27H,m,p-H 10,15,20-Ph), 7.50\u20137.49 (m, 6H,o,m-5-Ph), 7.34\u20137.33 (m, 3H,p-H, 5-Ph), 4.41 (s, 6H, \u2212CH2), \u22122.82 (s, 6H, \u2212NH). UV\u2013vis (THF): 420 (\u03b5 = 6.99 \u00d7 105mol\u20131dm3cm\u20131), 514 (\u03b5 = 3.06 \u00d7 104mol\u20131dm3cm\u20131), 549 (\u03b5 = 1.42 \u00d7 104mol\u20131dm3cm\u20131), 591 (\u03b5 = 8.72 \u00d7 103mol\u20131dm3cm\u20131), 647 (\u03b5 = 6.34 \u00d7 103mol\u20131dm3cm\u20131), 549 (\u03b5 = 1.42 \u00d7 104mol\u20131dm3cm\u20131), (\u03b5 = 1.16 \u00d7 103mol\u20131dm3cm\u20131)."},{"key":"ref21\/cit21b","unstructured":"General Procedure for the Preparation of zinc and manganese complexes3aand3b: The porphyrin triad3(0.100 g, 1 equiv) was dissolved in dimethoxyethane (DME), and an excess of the salt was added [for the zinc complex, zinc acetate (eight times) was used, and for the manganese complex, manganese acetate (10 times) was used]. The mixture was allowed to stand for 5 h at 70 \u00b0C (for zinc) and 80 \u00b0C (for manganese) and controlled by UV\u2013vis. The crude material was extracted with CH2Cl2\/water several times and dried with Na2SO4. The crude material was purified using silica gel column chromatography with CH2Cl2as the eluent.3a: 82 mg, 79%. HRMS (MALDI-TOF):m\/zcalcd2149.5093;m\/zfound2149.4940 ([M + H]+).1H NMR (300 MHz, CDCl3): \u03b4 8.82\u20138.69 (m, 24H, \u03b2-H), 8.23\u20138.02 (m, 18H,o-H, 10,15,20-Ph), 7.83 (s, 3H,o-H, 5-Ph), 7.77\u20137.52 (m, 27H,m,p-H, 10,15,20-Ph), 7.50\u20137.49 (m, 6H,o,m-5-Ph), 7.34\u20137.33 (m, 3H,p-H, 5-Ph), 4.41 (s, 6H, \u2212CH2). UV\u2013vis (THF): 424 (\u03b5 = 2.57 \u00d7 105mol\u20131dm3cm\u20131), 555 (\u03b5 = 1.13 \u00d7 104mol\u20131dm3cm\u20131), 595 (\u03b5 = 4 \u00d7 103mol\u20131dm3cm\u20131).3b: 72 mg, 74%. HRMS (MALDI-TOF):m\/zcalcd2259.1510,m\/zfound2259.1440 ([M + Na]+). UV\u2013vis (THF): 474 (\u03b5 = 1.11 \u00d7 104mol\u20131dm3cm\u20131), 583 (\u03b5 = 1.05 \u00d7 103mol\u20131dm3cm\u20131), 619 (\u03b5 = 1.16 \u00d7 103mol\u20131dm3cm\u20131)."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"1173","DOI":"10.1007\/s00894-007-0233-4","volume":"13","author":"Stewart J. J. P.","year":"2007","journal-title":"J. Mol. Model."},{"key":"ref23\/cit23","unstructured":"Web linkhttp:\/\/openmopac.net\/."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"4136","DOI":"10.1021\/ja809297a","volume":"131","author":"Reetz M. T.","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"1305","DOI":"10.1039\/C0CS00062K","volume":"40","author":"Thordarson P.","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref26\/cit26","doi-asserted-by":"crossref","first-page":"1295","DOI":"10.1021\/jp106822s","volume":"115","author":"Chylarecka D.","year":"2011","journal-title":"J. Phys. Chem. C"},{"key":"ref27\/cit27","doi-asserted-by":"crossref","first-page":"9433","DOI":"10.1021\/ac1020886","volume":"82","author":"Feng L. A.","year":"2010","journal-title":"Anal. Chem."}],"container-title":["Inorganic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/ic200727f","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,22]],"date-time":"2023-04-22T21:57:49Z","timestamp":1682200669000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/ic200727f"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,8,5]]},"references-count":27,"journal-issue":{"issue":"17","published-print":{"date-parts":[[2011,9,5]]}},"alternative-id":["10.1021\/ic200727f"],"URL":"https:\/\/doi.org\/10.1021\/ic200727f","relation":{},"ISSN":["0020-1669","1520-510X"],"issn-type":[{"value":"0020-1669","type":"print"},{"value":"1520-510X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,8,5]]}}}