Synthesis of porphyrins bearing trans-thiols

被引：30

作者：

Jagessar, RC

Tour, JM

机构：

[1] Rice Univ, Dept Chem, Houston, TX 77005 USA

[2] Rice Univ, Ctr Nanoscale Sci & Technol, Houston, TX 77005 USA

[3] Univ S Carolina, Dept Chem & Biochem, Columbia, SC 29208 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 02期

关键词：

D O I：

10.1021/ol9911728

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A route to porphyrins bearing trans-thiols is described using a thioacetyl containing aldehyde or a thioacetyl containing dipyrromethane in the presence of catalytic BF3. OEt2 followed by oxidation. Metal complexation and ammonium hydroxide induced acetyl removal provides a route to these important molecular systems for future electronics experiments in which the thiols would serve as the adhesion points to gold probes.

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页码：111 / 113

页数：3

相关论文

共 24 条

[1]

Alder A. D., 1967, J ORG CHEM, V32, P476

[2] Evolution of strategies for self-assembly and hookup of molecule-based devices [J].

Allara, DL ;

Dunbar, TD ;

Weiss, PS ;

Bumm, LA ;

Cygan, MT ;

Tour, JM ;

Reinerth, WA ;

Yao, Y ;

Kozaki, M ;

Jones, L .

MOLECULAR ELECTRONICS: SCIENCE AND TECHNOLOGY, 1998, 852 :349-370

[3] FACILE SYNTHESIS OF ETHYNYLATED BENZOIC-ACID DERIVATIVES AND AROMATIC-COMPOUNDS VIA ETHYNYLTRIMETHYLSILANE [J].

AUSTIN, WB ;

BILOW, N ;

KELLEGHAN, WJ ;

LAU, KSY .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (11) :2280-2286

[4]

Aviram A., 1998, ANN NY ACAD SCI

[5] 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

[6] Placement of conjugated oligomers in an alkanethiol matrix by scanned probe microscope lithography [J].

Chen, J ;

Reed, MA ;

Asplund, CL ;

Cassell, AM ;

Myrick, ML ;

Rawlett, AM ;

Tour, JM ;

Van Patten, PG .

APPLIED PHYSICS LETTERS, 1999, 75 (05) :624-626

[7] Insertion, conductivity, and structures of conjugated organic oligomers in self-assembled alkanethiol monolayers on Au{111} [J].

Cygan, MT ;

Dunbar, TD ;

Arnold, JJ ;

Bumm, LA ;

Shedlock, NF ;

Burgin, TP ;

Jones, L ;

Allara, DL ;

Tour, JM ;

Weiss, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (12) :2721-2732

[8] Overview of nanoelectronic devices [J].

Goldhaber-Gordon, D ;

Montemerlo, MS ;

Love, JC ;

Opiteck, GJ ;

Ellenbogen, JC .

PROCEEDINGS OF THE IEEE, 1997, 85 (04) :521-540

[9]

JOACHIM C, 1997, ATOMIC MOL WIRES

[10] Rapid solution and solid phase syntheses of oligo(1,4-phenylene ethynylene)s with thioester termini: Molecular scale wires with alligator clips. Derivation of iterative reaction efficiencies on a polymer support [J].

Jones, L ;

Schumm, JS ;

Tour, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1388-1410