{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2023,9,13]],"date-time":"2023-09-13T05:15:04Z","timestamp":1694582104824},"reference-count":26,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2015,6,25]],"date-time":"2015-06-25T00:00:00Z","timestamp":1435190400000},"content-version":"vor","delay-in-days":24,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Macromolecular Symposia"],"published-print":{"date-parts":[[2015,6]]},"abstract":"<jats:title>Summary<\/jats:title><jats:sec><jats:label \/><jats:p>New homoditopic bis\u2010calix[4]arene\u2010carbazole conjugates, armed with hydrophilic carboxylic acid functions at their lower rims, are disclosed. Evidence for their self\u2010association in solution was gathered from solvatochromic and thermochromic studies, as well as from gel\u2010permeation chromatography analysis. Their ability to function as highly sensitive sensors toward polar electron\u2010deficient aromatic compounds is demonstrated.<\/jats:p><\/jats:sec>","DOI":"10.1002\/masy.201400166","type":"journal-article","created":{"date-parts":[[2015,6,27]],"date-time":"2015-06-27T01:50:01Z","timestamp":1435369801000},"page":"87-94","source":"Crossref","is-referenced-by-count":1,"title":["Aryleneethynylene Trimers Bearing Calix[4]arenes: Synthesis, Optical Properties and Self\u2010Assembling Studies"],"prefix":"10.1002","volume":"352","author":[{"given":"Jos\u00e9 V.","family":"Prata","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica, \u00c1rea Departamental de Engenharia Qu\u00edmica and Centro de Investiga\u00e7\u00e3o de Engenharia Qu\u00edmica e Biotecnologia Instituto Superior de Engenharia de Lisboa, Instituto Polit\u00e9cnico de Lisboa R. Conselheiro Em\u00eddio Navarro, 1 1959\u2010007 Lisboa Portugal"}]},{"given":"Patr\u00edcia D.","family":"Barata","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Org\u00e2nica, \u00c1rea Departamental de Engenharia Qu\u00edmica and Centro de Investiga\u00e7\u00e3o de Engenharia Qu\u00edmica e Biotecnologia Instituto Superior de Engenharia de Lisboa, Instituto Polit\u00e9cnico de Lisboa R. Conselheiro Em\u00eddio Navarro, 1 1959\u2010007 Lisboa Portugal"}]}],"member":"311","published-online":{"date-parts":[[2015,6,25]]},"reference":[{"key":"e_1_2_5_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr990125q"},{"key":"e_1_2_5_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr900181u"},{"key":"e_1_2_5_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar500033n"},{"key":"e_1_2_5_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar5000456"},{"key":"e_1_2_5_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cs35075k"},{"key":"e_1_2_5_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/b501804h"},{"key":"e_1_2_5_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/cm102772x"},{"key":"e_1_2_5_8_1","doi-asserted-by":"crossref","DOI":"10.1007\/0-306-47522-7","volume-title":"Calixarenes 2001","author":"Asfari Z.","year":"2001"},{"key":"e_1_2_5_9_1","unstructured":"C. D. Gutsche \u201cCalixarenes: An Introduction\u201d 2nd ed. \u2013 MonographsinSupramolecular Chemistry J. F. Stoddart (Ed.) The Royal Society of Chemistry Cambridge2008."},{"key":"e_1_2_5_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.201300280"},{"key":"e_1_2_5_11_1","doi-asserted-by":"publisher","DOI":"10.1080\/10610278.2013.804185"},{"key":"e_1_2_5_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.09.109"},{"key":"e_1_2_5_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4PY00729H"},{"key":"e_1_2_5_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)02356-X"},{"key":"e_1_2_5_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/pola.22957"},{"key":"e_1_2_5_16_1","unstructured":"All new compounds (1 2 4\u20106) were characterized by spectroscopic techniques (FT\u2010IR 1H\/13C NMR) and microanalysis and full agreement with the proposed structures was found. Representative1H NMR (\u03b4\/ppm; CDCl3 400\u2009MHz) and elemental analysis data for compounds5and6are as follow; Calixarene5: 0.88 (s 18H \u2010C(CH3)3) 0.98 (s 18H \u2010C(CH3)3) 0.99 (t J=7.5\u2009Hz 6H \u2010N\u2010CH2CH2CH3 partially overlapped) 1.17 (s 36H \u2010C(CH3)3) 1.85\u20102.02 (m 4H \u2010N\u2010CH2CH2CH3) 3.17 (d J=12.8\u2009Hz 4H ArCHeqHAr) 3.19 (d J=13.0\u2009Hz 4H ArCHeqHAr) 3.52 (s 12H \u2010OCH3) 3.67 (s 6H \u2010OCH3) 4.30 (t J=6.6\u2009Hz 4H \u2010N\u2010CH2CH2CH3) 4.67 (s 4H ArOCH2Ar) 4.79 (d J=13.2\u2009Hz 4H ArCHHaxAr) 4.85 (d J=13.1\u2009Hz 4H ArCHHaxAr) 4.94 (d J=17.4\u2009Hz 4H ArOCHHCO2Me) 5.01 (d J=17.2\u2009Hz 4H ArOCHHCO2Me) 5.32 (s 4H ArOCH2CO2Me) 6.59 (s 4H calix\u2010ArH) 6.65 (s 4H calix\u2010ArH) 6.91 (s 8H calix\u2010ArH) 7.20\u20107.26 (m 2H ArC(6)H(cbz); partially overlapped with CHCl3) 7.37 (d J=8.0\u2009Hz 2H ArC(3)H(cbz)) 7.42 (d J=8.0\u2009Hz 2H ArC(8)H(cbz)) 7.43\u20107.52 (m 2H ArC(7)H(cbz)) 7.64 (s 2H ArC(1)H(cbz)) 8.02 (s 2H H\u2010Ar(\u2010C\u2261C\u2010)2\u2010H) 8.04 (d J=8.0\u2009Hz 2H ArC(4)H(cbz)) 8.08 (d J=7.7\u2009Hz 2H ArC(5)H(cbz)). Anal. Calcd. for C148H168N2O20: C 77.46; H 7.38; N 1.22; O 13.94. Found: C 77.61; H 7.53 N 1.42. Calixarene6: 0.87 (s 18H \u2010C(CH3)3) 0.97 (s 18H \u2010C(CH3)3) 0.99 (t J=7.6\u2009Hz 6H \u2010N\u2010CH2CH2CH3; partially overlapped) 1.17 (s 36H \u2010C(CH3)3) 1.87\u20101.99 (m 4H \u2010N\u2010CH2CH2CH3) 3.191 (d J=12.7\u2009Hz 4H ArCHeqHAr) 3.194 (d J=12.8\u2009Hz 4H ArCHeqHAr) 3.53 (s 12H \u2010OCH3) 3.68 (s 6H \u2010OCH3) 4.29 (t J=7.1\u2009Hz 4H \u2010N\u2010CH2CH2CH3) 4.68 (s 4H ArOCH2Ar) 4.80 (d J=12.9\u2009Hz 4H ArCHHaxAr) 4.88 (d J=12.8\u2009Hz 4H ArCHHaxAr) 4.96 (d J=16.6\u2009Hz 4H ArOCHHCO2Me) 5.04 (d J=16.5\u2009Hz 4H ArOCHHCO2Me) 5.33 (s 4H ArOCH2CO2Me) 6.59 (s 4H calix\u2010ArH) 6.65 (s 4H calix\u2010ArH) 6.92 (bs 8H calix\u2010ArH) 7.22\u20107.30 (m 2H ArC(6)H(cbz); partially overlapped with CHCl3) 7.36 (d J=8.5\u2009Hz 2H ArC(1)H(cbz)) 7.42 (d J=8.1\u2009Hz 2H ArC(8)H(cbz)) 7.45\u20107.53 (m 2H ArC(7)H(cbz)) 7.59 (dd J=8.5\u2009Hz J=1.3\u2009Hz 2H ArC(2)H(cbz)) 7.98 (s 2H H\u2010Ar(\u2010C\u2261C\u2010)2\u2010H) 8.13 (d J=7.8\u2009Hz 2H ArC(5)H(cbz)) 8.27 (d J=1.2\u2009Hz 2H ArC(4)H(cbz)). Anal. Calcd. for C148H168N2O20: C 77.46; H 7.38; N 1.22; O 13.94. Found: C 77.18; H 7.69 N 1.37. Structural assignments of5and6were based in 2D\u2010NMR spectroscopy techniques (COSY NOESY HSCQ and HMBC)."},{"key":"e_1_2_5_17_1","unstructured":"Representative1H NMR (\u03b4\/ppm; CDCl3 300 or 400\u2009MHz) and elemental analysis data for compounds1and2are as follow; Calixarene1: 0.81 (s 18H \u2010C(CH3)3) 0.87 (s 18H \u2010C(CH3)3) 0.91 (t J=7.4\u2009Hz 6H \u2010N\u2010CH2CH2CH3 ) 1.28 (s 36H \u2010C(CH3)3) 1.76\u20101.87 (m 4H \u2010N\u2010CH2CH2CH3) 3.23 (d J=12.7\u2009Hz 4H ArCHeqHAr) 3.35 (d J=12.3\u2009Hz 4H ArCHeqHAr) 4.21 (t J=7.2\u2009Hz 4H \u2010N\u2010CH2CH2CH3) 4.34 (s 4H ArOCH2Ar) 4.40 (d J=12.7\u2009Hz 4H ArCHHaxAr) 4.72 (d J=16.6\u2009Hz 4H ArOCHHCO2H) 4.83\u20105.27 (m 12H ArCHHaxAr (4H) ArOCHHCO2H (4H) ArOCH2CO2H (4H)) 6.56 (s 4H calix\u2010ArH) 6.59 (s 4H calix\u2010ArH) 7.09 (s 4H calix\u2010ArH) 7.12 (s 4H calix\u2010ArH) 7.19\u20107.26 (m 2H ArC(6)H(cbz); partially overlapped with CHCl3) 7.34\u20107.52 (m 6H ArC(3 7 8)H(cbz)) 7.67 (s 2H ArC(1)H(cbz)) 7.93\u20108.15 (m 6H H\u2010Ar(\u2010C\u2261C\u2010)2\u2010H ArC(4 5)H(cbz)). Anal. Calcd. for C142H156N2O20: C 77.15; H 7.11; N 1.27; O 14.47. Found: C 77.02; H 7.27 N 1.45. Calixarene2: 0.82 (s 18H \u2010C(CH3)3) 0.87 (s 18H \u2010C(CH3)3) 0.96 (t J=7.4\u2009Hz 6H \u2010N\u2010CH2CH2CH3) 1.29 (s 36H \u2010C(CH3)3) 1.84\u20101.95 (m 4H \u2010N\u2010CH2CH2CH3) 3.22 (d J=12.9\u2009Hz 4H ArCHeqHAr) 3.41 (bd J=12.4\u2009Hz 4H ArCHeqHAr) 4.25 (t J=7.0\u2009Hz 4H \u2010N\u2010CH2CH2CH3) 4.33 (bs 4H ArOCH2Ar) 4.37 (d J=12.6\u2009Hz 4H ArCHHaxAr) 4.65 (d J=15.8\u2009Hz 4H ArOCHHCO2H) 5.00\u20105.12 (m 8H ArOCHHCO2H (4H) ArOCH2CO2H (4H)) 5.16 (d J=12.6\u2009Hz 4H ArCHHaxAr) 6.54 (s 4H calix\u2010ArH) 6.59 (s 4H calix\u2010ArH) 7.11 (s 4H calix\u2010ArH) 7.13 (s 4H calix\u2010ArH) 7.22\u20107.30 (m 2H ArC(6)H(cbz); partially overlapped with CHCl3) 7.33 (d J=8.3\u2009Hz 2H ArC(1)H(cbz)) 7.39 (d J=8.4\u2009Hz 2H ArC(8)H(cbz)) 7.44\u20107.50 (m 2H ArC(7)H(cbz)) 7.70 (d J=8.0\u2009Hz 2H ArC(2)H(cbz)) 8.00 (s 2H H\u2010Ar(\u2010C\u2261C\u2010)2\u2010H) 8.08 (d J=7.9\u2009Hz 2H ArC(5)H(cbz)) 8.33 (s 2H ArC(4)H(cbz)). Anal. Calcd. for C142H156N2O20.H2O: C 76.50; H 7.14; N 1.26; O 15.07. Found: C 76.09; H 7.32 N 1.44. The presence of water was qualitatively confirmed in the1H NMR spectrum of similarly dried samples. Signals corresponding to carboxylic acid protons were not discernible in the spectra. Structural assignments of1and2were based in 2D\u2010NMR spectroscopy techniques (COSY NOESY HSCQ and HMBC)."},{"key":"e_1_2_5_18_1","unstructured":"The fluorescence quantum yields of1and2were determined [19] in CHCl3using 9 10\u2010diphenylanthracene as reference (\u03a6F\u2009=\u20090.72 ethanol) in air\u2010equilibrated conditions (\u03bbexc\u2009=\u2009360\u2009nm; right angle geometry in 1\u2010cm quartz cells) keeping the optical densities of the samples and reference below 0.05 at the excitation wavelength to prevent inner filter effects."},{"key":"e_1_2_5_19_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac198860071107"},{"key":"e_1_2_5_20_1","unstructured":"Assuming a static quenching mechanism F0\/F=1+KSV[Q] where F0and F are the fluorescence intensities of the fluorophore in the absence and presence of the quencher (Q) and [Q] is the quencher concentration.[21]The association constant for complex formation (K=[FQ]\/[F][Q]) isKSV."},{"key":"e_1_2_5_21_1","doi-asserted-by":"publisher","DOI":"10.1007\/978-0-387-46312-4_8"},{"key":"e_1_2_5_22_1","unstructured":"The correctedKSVswere determined from the equation (F0\/F)\u03b7=1+Ksv[Q] where \u03b7 is the correction factor for inner\u2010filter effects calculated in accordance to ref. 23."},{"key":"e_1_2_5_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2313(98)00063-5"},{"key":"e_1_2_5_24_1","unstructured":"The LUMO energy levels of PA and TNT determined from DFT calculations run at the B3LYP\/6\u2010311G* level of theory[25]in vacuo are \u22124.03\u2009eV and \u22123.65\u2009eV respectively."},{"key":"e_1_2_5_25_1","unstructured":"Spartan'04 Molecular Modeling Program Wavefunction Inc. Irvine CA 2005."},{"key":"e_1_2_5_26_1","unstructured":"For a discussion of this phenomenon and also for pertinent references on this topic see ref. [13]."}],"container-title":["Macromolecular Symposia"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fmasy.201400166","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/masy.201400166","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,12]],"date-time":"2023-09-12T02:50:35Z","timestamp":1694487035000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/masy.201400166"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,6]]},"references-count":26,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2015,6]]}},"alternative-id":["10.1002\/masy.201400166"],"URL":"https:\/\/doi.org\/10.1002\/masy.201400166","archive":["Portico"],"relation":{},"ISSN":["1022-1360","1521-3900"],"issn-type":[{"value":"1022-1360","type":"print"},{"value":"1521-3900","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,6]]}}}