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On-line Access: 2016-02-02

Received: 2015-07-22

Revision Accepted: 2015-10-08

Crosschecked: 2016-01-25

Cited: 1

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Citations:  Bibtex RefMan EndNote GB/T7714


Hao-jie Yu


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Journal of Zhejiang University SCIENCE A 2016 Vol.17 No.2 P.144-154


Synthesis of ferrocene- and azobenzene-based compounds for anion recognition

Author(s):  Xiao-ting Zhai, Hao-jie Yu, Li Wang, Zheng Deng, Zain-ul Abdin, Yong-sheng Chen

Affiliation(s):  The State Key Laboratory of Chemical Engineering, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China

Corresponding email(s):   hjyu@zju.edu.cn, opl_wl@dial.zju.edu.cn

Key Words:  Ferrocene, Azobenzene, Hydrogen bonding, High density information storage, Anion recognition

Xiao-ting Zhai, Hao-jie Yu, Li Wang, Zheng Deng, Zain-ul Abdin, Yong-sheng Chen. Synthesis of ferrocene- and azobenzene-based compounds for anion recognition[J]. Journal of Zhejiang University Science A, 2016, 17(2): 144-154.

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author="Xiao-ting Zhai, Hao-jie Yu, Li Wang, Zheng Deng, Zain-ul Abdin, Yong-sheng Chen",
journal="Journal of Zhejiang University Science A",
publisher="Zhejiang University Press & Springer",

%0 Journal Article
%T Synthesis of ferrocene- and azobenzene-based compounds for anion recognition
%A Xiao-ting Zhai
%A Hao-jie Yu
%A Li Wang
%A Zheng Deng
%A Zain-ul Abdin
%A Yong-sheng Chen
%J Journal of Zhejiang University SCIENCE A
%V 17
%N 2
%P 144-154
%@ 1673-565X
%D 2016
%I Zhejiang University Press & Springer
%DOI 10.1631/jzus.A1500183

T1 - Synthesis of ferrocene- and azobenzene-based compounds for anion recognition
A1 - Xiao-ting Zhai
A1 - Hao-jie Yu
A1 - Li Wang
A1 - Zheng Deng
A1 - Zain-ul Abdin
A1 - Yong-sheng Chen
J0 - Journal of Zhejiang University Science A
VL - 17
IS - 2
SP - 144
EP - 154
%@ 1673-565X
Y1 - 2016
PB - Zhejiang University Press & Springer
ER -
DOI - 10.1631/jzus.A1500183

A series of ferrocene- and azobenzene-based compounds with acyl amine groups attached were designed and synthesized to explore their potential application in anion recognition. Their electro- and photo-properties, and the effect of nitro and amine substituents of the benzene ring on anion recognition were studied by UV-vis absorption spectroscopy (UV) and cyclic voltammetry (CV). The results showed that a nitro group substituent has a positive effect on the binding affinity and sensitivity, which might be due to the strong hydrogen bonding interaction between the receptor and the guest, while an amino group substituent has a negative effect on the sensitivity. Furthermore, the shift in the UV-vis absorption spectra was observed as a color change, which can be used for the naked-eye detection of F and H2PO4.

This paper describes the design, preparation and anion recognition property study of three ferrocene and azobenzene based compounds. While the synthesis is simple and straightforward, the resulting compounds showed promising and interesting selective recognition of anions. I think this article nicely describes the design and synthesis of ferrocene chromophore system and evaluate the products as potential ion detectors. I thought the synthesis was presented in a fashion that is not in the traditional synthetic experimental style where the produce for all new compounds are presented followed by a list of the spectral data (e.g., Rf, mp, IR, 1H NMR, 13CNMR and HRMS) for new all new compounds.


目的:研究二茂铁基偶氮苯化合物的光电响应性能及 离子识别性能,并研究取代基对其离子识别性能的影响。


Darkslateblue:Affiliate; Royal Blue:Author; Turquoise:Article


[1]Amer, W.A., Yu, H.J., Wang, L., et al., 2013. Synthesis, characterization and properties of some main-chain ferrocene-based polymers containing aromatic units. Journal of Inorganic and Organometallic Polymers and Materials, 23(6):1431-1444.

[2]Apreutesei, D., Mehl, G.H., Scutaru, D., 2007. Ferrocene-containing liquid crystals bearing a cholesteryl unit. Liquid Crystals, 34(7):819-831.

[3]Beer, P.D., Graydon, A.R., Johnson, A., et al., 1997. Neutral ferrocenoyl receptors for the selective recognition and sensing of anionic guests. Inorganic Chemistry, 36(10):2112-2118.

[4]Carlescu, I., Scutaru, A.M., Apreutesei, D., et al., 2007. The liquid crystalline behaviour of ferrocene derivatives containing azo and imine linking groups. Liquid Crystals, 34(7):775-785.

[5]Deng, L.B., Wang, L., Huo, J., et al., 2008. Preparation of N,N′-bisethoxyethane[12]amideferrocenophane and its application in anion recognition. Journal of Physical Chemistry B, 112(17):5333-5337.

[6]Ikeda, T., Tsutsumi, O., 1995. Optical switching and image storage by means of azobenzene liquid-crystal films. Science, 268(5219):1873-1875.

[7]Kumar, G.S., Neckers, D.C., 1989. Photochemistry of azobenzene-containing polymers. Chemical Reviews, 89(8):1915-1925.

[8]Kuo, L.J., Liao, J.H., Chen, C.T., et al., 2003. Two-arm ferrocene amide compounds: synclinal conformations for selective sensing of dihydrogen phosphate ion. Organic Letters, 5(11):1821-1824.

[9]Kurihara, M., Hirooka, A., Kume, S., et al., 2002. Redoxconjugated reversible isomerization of ferrocenyl-azobenzene with a single green light. Journal of the American Chemical Society, 124(30):8800-8801.

[10]Kurosawa, M., Takuya, N., Takayuki, M., et al., 1999. Synthesis of azo-bridged ferrocene oligomers and a polymer and electrochemical and optical analysis of internuclear electronic interactions in their mixed-valence states. Inorganic Chemistry, 38(22):5113-5123.

[11]Li, C., Wang, L., Yu, H.J., et al., 2013. Synthesis of novel colorimetric probe molecules and their application in anion recognition based on strong hydrogen bond. Journal of Organometallic Chemistry, 726:32-36.

[12]Lisa, G., Wilson, D.A., Scutaru, D., et al., 2010. Investigation of thermal degradation of some ferrocene liquid crystals. Thermochimica Acta, 507-508(8):49-59.

[13]Manners, I., 1999. Poly(ferrocenylsilanes): novel organometallic plastics. Chemical Communications, (10):857-865.

[14]Miyaji, H., Collinson, S.R., Prokes I., et al., 2003. A ditopic ferrocene receptor for anions and cations that functions as a chromogenic molecular switch. Chemical Communications, (1):64-65.

[15]Muraoka, T., Kinbara, K., Aida, T., 2006. Mechanical twisting of a guest by a photoresponsive host. Nature, 440(7083):512-515.

[16]Muraoka, T., Kinbara, K., Aida, T., 2007. Reversible operation of chiral molecular scissors by redox and UV light. Chemical Communications, (14):1441-1443.

[17]Namiki, K., Murata, M., Kume, S., et al., 2011. Synthesis of photo-switchable 3-FcAB-modified polymer particles. New Journal of Chemistry, 35(10):2146-2152.

[18]Natansohn, A., Rochon, P., 2002. Photoinduced motions in azo-containing polymers. Chemical Reviews, 102(11):4139-4175.

[19]Onofrei, R.M., Carlescu, I., Lisa, G., et al., 2012. Synthesis and liquid crystalline behavior of some monosubstituted ferrocene containing schiff bases. Revista De Chimie, 63(2):139-145.

[20]Onofrei, R.M., Carlescu, I., Epure, L., et al., 2013. Synthesis and liquid crystalline properties of some esters of 4-ferrocenyl-4′-hydroxyazobenzene. Acta Chimica Slovenica, 60(3):604-616.

[21]Oton, F., Tarraga, A., Velasco, M., et al., 2004. A new fluoride selective electrochemical and fluorescent chemosensor based on a ferrocene-naphthalene dyad. Chemical Communications, 14:1658-1659.

[22]Reynes, O., Bucher, C., Moutet, J.C., et al., 2004. Redox sensing of anions in pure aqueous environment by ferrocene-containing 4,4′-bipyridinium-based receptors and polymer films. Chemical Communications, 4:428-429.

[23]Sakamoto, A., Hirooka, A., Namiki, K., et al., 2005. Photon-, electron-, and proton-induced isomerization behavior of ferrocenylazobenzenes. Inorganic Chemistry, 44(21):7547-7558.

[24]Seibold, E.A., Sutton, L.E., 1955. Structure of ferrocene. Journal of Chemical Physics, 23(10):1967.

[25]Shafir, A., Power, M.P., Whitener, G.D., et al., 2000. Synthesis, structure, and properties of 1,1′-diamino- and 1,1′-diazidoferrocene. Organometallics, 19(19):3978-3982.

[26]Sola, A., Tarraga, A., Molina, P., 2012. A ferrocenyl-guanidine derivative as a highly selective electrochemical and colorimetric chemosensor molecule for acetate anions. Dalton Transactions, 41(27):8401-8409.

[27]Szymanska, I., Radecka, H., Radecki, J., et al., 2006. Ferrocene-substituted calix[4]pyrrole modified carbon paste electrodes for anion detection in water. Journal of Electroanalytical Chemistry, 591(2):223-228.

[28]Tan, Q.H., Wang, L., Yu, H.J., et al., 2007. Study on synthesis and electrochemical properties of a novel ferrocene-based compound and its application in anion recognition. Journal of Physical Chemistry B, 111(15):3904-3909.

[29]Tan, Q.H., Wang, L., Ma, L., et al., 2008. Study on anion electrochemical recognition based on a novel ferrocenyl compound with multiple binding sites. Journal of Physical Chemistry B, 112(35):11171-11176.

[30]Tan, Q.H., Wang, L., Ma, L., et al., 2009. Electrochemical behaviors and anion recognition of ferrocene modified hyperbranched polyether. Macromolecules, 42(13):4500-4510.

[31]Thomas, J.L., Howarth, J., Hanlon, K., et al., 2000. Ferrocenyl imidazolium salts as a new class of anion receptors with C-H center dot center dot center dot X-hydrogen bonding. Tetrahedron Letters, 41(3):413-416.

[32]Villoslada, R., Alonso, B., Casado, C.M., et al., 2009. Anion receptor electrochemical sensing properties of poly(propyleneimine) dendrimers with ferrocenylamidoalkyl terminal groups. Organometallics, 28(3):727-733.

[33]Yoon, J., Kim, S.K., Singh, N.J., et al., 2006. Imidazolium receptors for the recognition of anions. Chemical Society Reviews, 35(4):355-360.

[34]Zheng, W.R., Li, J., Huang, T., et al., 2011. Hydrogen bonding interaction between ureas or thioureas and nitro-compounds. Research on Chemical Intermediates, 37(1):31-45.

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