Synthesis and Acidichromic and Ionochromic Properties of Bisindolinospiropyran

doi:10.3724/SP.J.1095.2014.30406

Chinese Journal of Applied Chemistry

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Synthesis and Acidichromic and Ionochromic Properties of Bisindolinospiropyran

LIU Hui¹, LI Linglan^2*,YE Chuping²

(1.National Engineering Research Center for New Polymer Formed Equipment of
South China University of Technology,Guangzhou 510640,China;
2.College of Chemistry and Chemical Engineering,Hubei University,Wuhan 430062,China)

Received:2013-08-08 Revised:2013-09-28 Published:2014-06-10 Online:2014-06-10
Contact: Linglan Li

Abstract

Abstract: The design, synthesis, and structural characterization of a novel bisindolinospiropyran(1) was reported. The acidichromic and ionochromic properties of compound 1 were investigated. The results indicate that compound 1 possesses an interesting ring opening reaction with the addition of proton or several metal ions in isopropanol. Upon addition of hydrogen or metal ions(Fe3+, Al3+ and Cu2+), compound 1 shows a new absorption spectra peak around 460 nm, and the color of the solution changes from colorless to red. The color and absorption spectra of this compound can be restored when the hydroxide ions or EDTA is added. These properties can be applied to molecular sensors and ion recognition.

Key words: acidichromism, ionochromism, indolinospiropyran, sensor, ion recognition

CLC Number:

O621.2

LIU Hui1, LI Linglan2*, YE Chuping2. Synthesis and Acidichromic and Ionochromic Properties of Bisindolinospiropyran[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30406.

References

[1] Wang S,Hwang I J,Gwon S Y,et al. Ionochromism of Crystal Violet Lactone Triggered by Metal Cations[J]. Fiber Polym,2010,11(8):1198-1200.

[2] Pinheiro C,Parola A J,Pina F,et al. Electrochromism of Crystal Violet Lactone in the Presence of Fe(Ⅲ)/Fe(Ⅱ) Redox Rair[J]. Electrochim Acta,2009,54(23):5593-5597.

[3] Siri O,Braunstein P,Rohmer M M,et al. Novel “Potentially Antiaromatic”, Acidichromic Quinonediimines with Tunable Delocalization of Their 6 Pi-electron Subunits[J]. J Am Chem Soc,2003,125(45):13793-13803.

[4] Yin M F,Gong H F,Zhang B W,et al. Photochemical Reaction, Acidichromism, and Supramolecular Nanoarchitectures in the Langmuir-Blodgett Films of an Amphiphilic Styrylquinoxaline Derivative[J]. Langmuir,2004,20(19):8042-8048.

[5] Wang S,Gwon S Y,Kim S H. A Highly Selective and Sensitive Colorimetric Chemosensor for Fe2+ Based on Fluoran Dye[J]. Spectrochim Acta A,2010,76(3/4):293-296.

[6] Patel R G,Patel M P,Patel R G. Synthesis and Characterization of Chromogenic Fluoran Compounds Containing 4-Ketoquinazolinone Moieties[J]. J Serb Chem Soc,2004,69(5):327-333.

[7] Liu Y H,Liu M H. Langmuir-Blodgett Film and Acidichromism of a Long Chain Carbazole-Containing Schiff Base[J]. Thin Solid Films,2002,415(1/2):248-252.

[8] Luo Q F,Li X C,Jing S P,et al. A Novel Bisthienylethene as Acidichromic and Photochromic Yellow Dye[J]. Chem Lett,2003,32(12):1116-1117.

[9] Lin S L,Kuo P Y,Yang D Y. Design and Synthesis of a Coumarin-Based Acidichromic Colorant[J]. Molecules,2007,12(7):1316-1324.

[10] Lin C T,Shih J H,Chen C L,et al. Synthesis of Novel Triketone-Based Acidichromic Colorants[J]. Tetrahedron Lett,2005,46(30):5033-5037.

[11] Burns C T,Choi S Y,Dietz M L,et al. Acidichromic Spiropyran-Functionalized Mesoporous Silica:Towards Stimuli-Responsive Metal ion Separations Media[J]. Sep Sci Technol,2008,43(9/10):2503-2519.

[12] Fan M G,Sun X D,Liang Y C,et al. “Acidichromics” of Photochromic Spirooxazines[J]. Mol Cryst Liq Cryst A,1997,297:305-312.

[13] Liang Y C,Ming Y F,Fan M G.,et al. Acidichromism of Indolinospirooxazines in Isopropanol[J]. Sci China Ser B,1997,40(5):535-540.

[14] Gentili P L. The Fundamental Fuzzy Logic Operators and Some Complex Boolean Logic Circuits Implemented by the Chromogenism of a Spirooxazine[J]. Phys Chem Chem Phys,2011,13(45):20335-20344.

[15] WANG Jianying,FENG Changgen. Progress on Synthesis of Photochromic Spirooxazines[J]. Chinese J Appl Chem,2007,24(7):729-736.

王建营,冯长根. 螺噁嗪类光致变色化合物的合成研究进展[J]. 应用化学,2007,24(7):729-736.

[16] LI Zhongjie,DONG Yigong. Synthesis and Photochromic Properties of Some 1-Octyl-3,3-Dimethylindolinospiropyrans[J]. Chinese J Appl Chem,2007,4(2):71-73.

李仲杰,董绮功. 某些1-辛基-3,3-二甲基吲哚啉螺苯并吡喃的合成和光致变色性质[J]. 应用化学,1987,4(2):71-73.

[17] ZHOU Qingqing,ZHANG Xianzhe,LIU Hewen. Synthesis and pH-Responsive Chromism of a Macrocyclic Compound with Three Spiropyran Units[J]. Chinese J Appl Chem,2012,29(16):1371-1380(in Chinese).

周清清,张宪哲,刘和文. 含三螺吡喃单元大环分子的合成和酸致变色效应[J]. 应用化学,2012,29(12): 1371-1380.

[18] Zhou Y C,Zhang D Q,Zhang Y Z,et al. Tuning the CD Spectrum and Optical Rotation Value of a New Binaphthalene Molecule with Two Spiropyran Units:Mimicking the Function of a Molecular “AND” Logic Gate and a New Chiral Molecular Switch[J]. J Org Chem,2005,70(16):6164-6170.

[19] Ren J Q,Tian H. Thermally Stable Merocyanine Form of Photochromic Spiropyran with Aluminum Ion as a Reversible Photo-driven Sensor in Aqueous Solution[J]. Sensors,2007,7(12):3166-3178.

[20] GU Liuyuan,TU Hui,ZHU Li,et al. Synthesis and Luminescent Properties of Novel Metal-organic Coordination Polymers Based on Bisphenol A[J]. Chinese J Lumin,2011,32(2):127-133(in Chinese).

谷刘园,屠慧,朱荔,等. 基于双酚A的希夫碱型锌配位聚合物的合成及发光性能[J]. 发光学报,2011,32(2):127-133.

Synthesis and Acidichromic and Ionochromic Properties of Bisindolinospiropyran

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