Synthesis and characterization of ferrocenyl-acridine dyads and their multiresponse to proton and metal cations

被引：21

作者：

Cao, Qian-Yong ^{[1
]}

Lu, Xin ^{[1
]}

Li, Zhi-Hua ^{[1
]}

Zhou, Li ^{[1
]}

Yang, Zhen-Yu ^{[1
]}

Liu, Jiang-Hua ^{[1
]}

机构：

[1] Nanchang Univ, Dept Chem, Nanchang 330031, Peoples R China

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2010年 / 695卷 / 09期

关键词：

Ferrocene; Acridine; Prontonation; Metal cations; Electrochemistry; Optical spectroscopy; CONJUGATED OLIGOMERS; ELECTRONIC-STRUCTURE; OPTICAL-PROPERTIES; NLO PROPERTIES; COMPLEXES; CHEMOSENSOR; DERIVATIVES; TRANSITION; ETHENYL; FLUORESCENCE;

D O I：

10.1016/j.jorganchem.2010.02.013

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two new pi-conjugated linked ferrocenyl-acridine dyads, (9-ethynylferrocenyl) acridine (3a) and (1-(ferrocenylethynyl)-4-ethynylbenzenyl)-acridine (3b), have been synthesized and investigated. UV-Vis spectroscopic and electrochemical studies reveal that 3a offers stronger electronic communication between terminal subunits than the extended system 3b, as shown by a stronger and lower-energy metal-toligand charge transfer (MLCT) transition and a more positive redox potential. Both of 3a and 3b show multiresponse to protons and selected metal ions (M = Zn2+, Pb2+, Hg2+, Fe3+, Cr3+), with a MLCT transition shift to the lower-energy, a redox potential shift to anode, and a luminescence increasing. (C) 2010 Elsevier B. V. All rights reserved.

引用

页码：1323 / 1327

页数：5

共 40 条

[1]

Albert A., 1955, Organic Syntheses, V3, P53

[2] Studies of the electronic structure of metallocene-based second-order nonlinear optical dyes [J].

Barlow, S ;

Bunting, HE ;

Ringham, C ;

Green, JC ;

Bublitz, GU ;

Boxer, SG ;

Perry, JW ;

Marder, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3715-3723

[3] Electronic and optical properties of conjugated group 8 metallocene derivatives [J].

Barlow, S ;

Marder, SR .

CHEMICAL COMMUNICATIONS, 2000, (17) :1555-1562

[4] Luminescent anion recognition: Selective induced emission by binding of dihydrogenphosphate [J].

Beer, PD ;

Graydon, AR ;

Sutton, LR .

POLYHEDRON, 1996, 15 (14) :2457-2461

[5] Anion selective recognition and sensing by novel macrocyclic transition metal receptor systems. H-1 NMR, electrochemical, and photophysical investigations [J].

Beer, PD ;

Szemes, F ;

Balzani, V ;

Sala, CM ;

Drew, MGB ;

Dent, SW ;

Maestri, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (49) :11864-11875

[6] Ferrocenyl-substituted fluorescent anthracenes and anthraquinones [J].

Butler, IR ;

Callabero, AG ;

Kelly, GA ;

Amey, JR ;

Kraemer, T ;

Thomas, DA ;

Light, ME ;

Gelbrich, T ;

Coles, SJ .

TETRAHEDRON LETTERS, 2004, 45 (03) :467-472

[7] Highly selective chromogenic and redox or fluorescent sensors of Hg2+ in aqueous environment based on 1,4-disubstituted azines [J].

Caballero, A ;

Martínez, R ;

Lloveras, V ;

Ratera, I ;

Vidal-Gancedo, J ;

Wurst, K ;

Tárraga, A ;

Molina, P ;

Veciana, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15666-15667

[8] Electroactive thiazole derivatives capped with ferrocenyl units showing charge-transfer transition and selective ion-sensing properties:: A combined experimental and theoretical study [J].

Caballero, Antonio ;

Lloveras, Vega ;

Curiel, David ;

Tarraga, Alberto ;

Espinosa, Arturo ;

Garcia, Rafaela ;

Vidal-Gancedo, Jose ;

Rovira, Concepcio ;

Wurst, Klaus ;

Molina, Pedro ;

Veciana, Jaume .

INORGANIC CHEMISTRY, 2007, 46 (03) :825-838

[9] Direct C-C coupling of ferrocenyllithium and azaheterocycles by nucleophilic substitution of hydrogen -: Synthesis of mono- and 1,1′-diazinylferrocenes [J].

Chupakhin, Oleg N. ;

Utepova, Irina A. ;

Kovalev, Igor S. ;

Rusinov, Vladimir L. ;

Starikova, Zoya A. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (05) :857-862

[10] Synthesis, structure, and redox chemistry of ethenyl and ethynyl ferrocene polyaromatic dyads [J].

Cuffe, L ;

Hudson, RDA ;

Gallagher, JF ;

Jennings, S ;

McAdam, CJ ;

Connelly, RBT ;

Manning, AR ;

Robinson, BH ;

Simpson, J .

ORGANOMETALLICS, 2005, 24 (09) :2051-2060

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