Macrocycles with a phenothiazine core: synthesis, structural analysis, and electronic properties

被引:6
作者
Medrut, Ilisca [1 ]
Turdean, Raluca [1 ]
Gropeanu, Radu [1 ]
Pop, Flavia [1 ]
Toupet, Loic [2 ]
Hadade, Niculina D. [1 ]
Bogdan, Elena [1 ]
Grosu, Ion [1 ]
机构
[1] Univ Babes Bolyai, Supramol Organ & Organometall Chem Ctr SOOMCC, Cluj Napoca 400028, Romania
[2] Univ Rennes 1, UMR 6626, F-35042 Rennes, France
关键词
Phenothiazines; Macrocycles; X-ray molecular structure; C-H ... pi interactions; ES-HRMS investigations; 1ST SYNTHESIS; CATION; COMPLEXATION; POLYMERS;
D O I
10.1016/j.tetlet.2012.12.068
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New phenothiazine macrocycles with polyethyleneoxy chains were synthesized in good yields by reacting 10-ethyl-10H-3,7-di(3-hydroxyphenyl)phenothiazine with diiodurated or ditosylated polyethyleneglycols. Their structures were investigated by NMR spectroscopy and single crystal X-ray crystallography in the case of one compound. The electronic properties were determined by absorption spectroscopy and cyclic voltammetry and their complexation ability for alkali cations was investigated by ES-HRMS. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1107 / 1111
页数:5
相关论文
共 41 条
[1]   THIONINE COATED ELECTRODE FOR PHOTOGALVANIC CELLS [J].
ALBERY, WJ ;
FOULDS, AW ;
HALL, KJ ;
HILLMAN, AR ;
EGDELL, RG ;
ORCHARD, AF .
NATURE, 1979, 282 (5741) :793-797
[2]   Electrospray ionization mass spectrometry (ESI-MS) as a useful tool for fast evaluation of anion and cation complexation abilities of a cyclam derivative [J].
Alfonso, I ;
Astorga, C ;
Gotor, V .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2005, 53 (1-2) :131-137
[3]  
Bauer H, 2001, EUR J ORG CHEM, V2001, P3255, DOI 10.1002/1099-0690(200109)2001:17<3255::AID-EJOC3255>3.0.CO
[4]  
2-0
[5]   CRYSTAL STRUCTURE OF PHENOTHIAZINE [J].
BELL, JD ;
BLOUNT, JF ;
BRISCOE, OV ;
FREEMAN, HC .
CHEMICAL COMMUNICATIONS, 1968, (24) :1656-&
[6]   Determination of binding selectivities in host-guest complexation by electrospray/quadrupole ion trap mass spectrometry [J].
Blair, SM ;
Kempen, EC ;
Brodbelt, JS .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 1998, 9 (10) :1049-1059
[7]  
Bodea C, 1968, Adv Heterocycl Chem, V9, P321, DOI 10.1016/S0065-2725(08)60375-X
[8]   First syntheses and electronic properties of (oligo)phenothiazine-C60 dyads [J].
Bucci, Nadine ;
Mueller, Thomas J. J. .
TETRAHEDRON LETTERS, 2006, 47 (47) :8323-8327
[9]   Synthesis and electronic properties of (oligo)phenothiazine-ethynyl-hydro-C60 dyads [J].
Bucci, Nadine ;
Mueller, Thomas J. J. .
TETRAHEDRON LETTERS, 2006, 47 (47) :8329-8332
[10]   Electro-optic property of chromophore-terminated trifunctional dendrimer in a guest-host system [J].
Cho, Min Ju ;
Lee, Sang Kyu ;
Jin, Jung-Il ;
Choi, Dong Hoon ;
Dalton, Larry R. .
THIN SOLID FILMS, 2006, 515 (04) :2303-2309