Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines

被引:15
作者
Franz, Adam W. [1 ]
Stoycheva, Svetlana [2 ]
Himmelhaus, Michael [2 ]
Mueller, Thomas J. J. [1 ]
机构
[1] Univ Dusseldorf, Inst Organ Chem & Makromol Chem, D-40225 Dusseldorf, Germany
[2] Heidelberg Univ, Inst Phys Chem, D-69120 Heidelberg, Germany
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 6卷
关键词
cyclic voltammetry; ellipsometry; phenothiazines; SAM; thiols; 1ST SYNTHESIS; MOLECULAR WIRES; SPECTROSCOPIC CHARACTERIZATION; ALLIGATOR CLIPS; RADICAL-CATION; MONOLAYERS; PHENOTHIAZINE; GOLD; ETHYNYLENE)S; CONDUCTANCE;
D O I
10.3762/bjoc.6.72
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(Oligo)phenothiazinyl thioacetates, synthesized by a one-pot sequence, are electrochemically oxidizable and highly fluorescent. SAMs can be readily formed from thiols prepared by in situ deprotection of the thioacetates in the presence of a gold-coated silicon wafer. Monolayer formation is confirmed by ellipsometry and the results compared to those obtained by force field and DFT calculations.
引用
收藏
页数:9
相关论文
共 65 条
[1]   Synthesis, Electronic Properties, and Self-Assembly on Au{111} of Thiolated Phenylethynyl Phenothiazines [J].
Barkschat, Christa S. ;
Stoycheva, Svetlana ;
Himmelhaus, Michael ;
Mueller, Thomas J. J. .
CHEMISTRY OF MATERIALS, 2010, 22 (01) :52-63
[2]   Butadiynyl-bridged Diphenothiazines - Redox-active Fluorophores and Self-assembly on HOPG [J].
Barkschat, Christa S. ;
Guckenberger, Reinhard ;
Mueller, Thomas J. J. .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2009, 64 (06) :707-718
[3]  
BECKER HGO, 1996, ORGANIKUM
[4]   A trinuclear EMAC-type molecular wire with redox-active ferrocenylacetylide "alligator clips" attached [J].
Berry, JF ;
Cotton, FA ;
Murillo, CA .
ORGANOMETALLICS, 2004, 23 (10) :2503-2506
[5]   First syntheses and electronic properties of (oligo)phenothiazine-C60 dyads [J].
Bucci, Nadine ;
Mueller, Thomas J. J. .
TETRAHEDRON LETTERS, 2006, 47 (47) :8323-8327
[6]   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
[7]   Are single molecular wires conducting? [J].
Bumm, LA ;
Arnold, JJ ;
Cygan, MT ;
Dunbar, TD ;
Burgin, TP ;
Jones, L ;
Allara, DL ;
Tour, JM ;
Weiss, PS .
SCIENCE, 1996, 271 (5256) :1705-1707
[8]   Synthesis of ladder polyaromatics as new molecular device candidates [J].
Ciszek, JW ;
Tour, JM .
TETRAHEDRON LETTERS, 2004, 45 (13) :2801-2803
[9]   Effects of hindered internal rotation on packing and conductance of self-assembled monolayers [J].
Dameron, AA ;
Ciszek, JW ;
Tour, JM ;
Weiss, PS .
JOURNAL OF PHYSICAL CHEMISTRY B, 2004, 108 (43) :16761-16767
[10]   Preparation of 3-substituted 10-methylphenothiazines [J].
Ebdrup, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (06) :1147-1150