Cation-induced π-stacking

被引：26

作者：

Bosch, Eric ^{[1
]}

Barnes, Charles L. ^{[2
]}

Brenrian, Nathan L. ^{[1
]}

Eakins, Galen L. ^{[1
]}

Breyfogle, Bryan E. ^{[1
]}

机构：

[1] Missouri State Univ, Dept Chem, Springfield, MO 65897 USA

[2] Univ Missouri, Dept Chem, Columbia, MO 65211 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 10期

关键词：

D O I：

10.1021/jo800343f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The design and synthesis of a new dipyridyl ligand with appended phenanthryl moieties is described. On addition of increments of silver(I) trifluoromethanesulfonate to a solution of the ligand, the phenanthryl protons shift upfield in the H-1 NMR spectrum, suggesting that the phenanthrenes pi-stack on coordination of silver(I). In accord with this, the oxidation potential decreased from 1.74 to 1.55 V on complexation of silver(l). The pi-stacking was confirmed with the single-crystal X-ray structure of a palladium(II) coordination complex.

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页码：3931 / 3934

页数：4

相关论文

共 24 条

[1]

Adams H, 2001, CHEM-EUR J, V7, P4863, DOI 10.1002/1521-3765(20011119)7:22<4863::AID-CHEM4863>3.0.CO

[2]

2-3

[3] AROMATIC MOLECULAR CMPLEXES OF THE ELECTRON DONOR-ACCEPTOR TYPE [J].

ANDREWS, LJ .

CHEMICAL REVIEWS, 1954, 54 (05) :713-776

[4] 1,2-bis(2-pyridylethynyl) benzene, a novel trans-chelating bipyridyl ligand. Structural characterization of the complexes with silver(I) triflate and palladium(II) chloride [J].

Bosch, E ;

Barnes, CL .

INORGANIC CHEMISTRY, 2001, 40 (13) :3097-3100

[5] CRYSTAL-STRUCTURES OF POLYNUCLEAR AROMATIC-HYDROCARBONS - CLASSIFICATION, RATIONALIZATION AND PREDICTION FROM MOLECULAR-STRUCTURE [J].

DESIRAJU, GR ;

GAVEZZOTTI, A .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1989, 45 :473-482

[6] Attractions and repulsions in molecular crystals: What can be learned from the crystal structures of condensed ring aromatic hydrocarbons? [J].

Dunitz, JD ;

Gavezzotti, A .

ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (08) :677-684

[7] Three unique coordination geometries involving 1,2-dimethoxy-4,5-bis(2-pyridylethynyl)benzene [J].

Fiscus, JE ;

Shotwell, S ;

Layland, RC ;

Smith, MD ;

zur Loye, HC ;

Bunz, UHF .

CHEMICAL COMMUNICATIONS, 2001, (24) :2674-2675

[8] A test for homology: Photoactive crystalline assemblies involving linear templates based on a homologous series of phloroglucinols [J].

Friscic, T ;

Drab, DM ;

MacGillivray, LR .

ORGANIC LETTERS, 2004, 6 (25) :4647-4650

[9] Synthetic supramolecular chemistry [J].

Fyfe, MCT ;

Stoddart, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (10) :393-401

[10] A SYSTEMATIC ANALYSIS OF PACKING ENERGIES AND OTHER PACKING PARAMETERS FOR FUSED-RING AROMATIC-HYDROCARBONS [J].

GAVEZZOTTI, A ;

DESIRAJU, GR .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1988, 44 :427-434