Anion Probe and Molecular Logic Gate Based on Tryptanthrin Derivative†

doi:10.7503/cjcu20140090

Abstract

Abstract:

A tryptanthrin derivative as anions probe was synthesized by the reaction of tryptanthrin with phenylhydrazine. In DMF, with the addition of F^-, AcO^- and H₂P $O 4 -$ , the “yellow-to-orange” change could be observed by naked eyes. Meanwhile, there were no changes when other anions(Cl^-, Br^-, I^-, Cl $O 4 -$ , N $O 3 -$ and HS $O 4 -$ ) were added. ¹H NMR titrations of this anions probe indicated that the “yellow-to-orange” response was triggered by the hydrogen bonding interaction between NH with F^-, AcO^- and H₂P $O 4 -$ . Then a novel four-input molecular logic gate was designed.

Key words: Anion, Tryptanthrin, Molecular logic gate(Ed.: P, H, N, K)

CLC Number:

O657.32

TrendMD:

WANG Qingguo, LI Dan, LU Ning, TONG Dingyi, ZHUANG Hejing, LI Fuqiu, WANG Lan, DUAN Haifeng, LIN Yingjie. Anion Probe and Molecular Logic Gate Based on Tryptanthrin Derivative^†[J]. Chem. J. Chinese Universities, 2014, 35(10): 2114.

Figures/Tables 4

Scheme 1 Synthesis route of tryptanthrin derivative(probe)

Fig.1 Results after the addition of anions(250 μmol/L) (A) UV-Vis absorption changes of probe(25 μmol/L) in DMF; (B) A520 nm/A442 nm changes; (C) photo of the mixtures in DMSO.

Fig.2 Absorption spectra of probe(25 μmol/L) in DMF after adding different concentrations of anions(0—250 μmol/L)

Fig.3 Molecular logic system

References 27

[1]	de Silva A. P., Gunaratne H. Q. N., McCoy C. P., Nature,1993, 364, 42—44
[2]	de Silva A. P., Chem. Asian J., 2011, 6, 750—766
[3]	de Ruiter G., van der Boom M. E., Accounts Chem. Res., 2011, 44, 563—573
[4]	Zhang G. X., Zhang D. Q., Journal of Chemical Education,2012, 9, 19—21
	(张关心, 张德清. 化学教育, 2012, 9, 19—21)
[5]	Pischel U., Andreasson J., Gust D., Pais V. F., ChemPhysChem,2013, 14, 28—46
[6]	Gentili P. L., RSC Adv., 2013, 3, 25523—25549
[7]	Banerjee A., Sahana A., Das S., Lohar S., Sarkar B., Mukhopadhyay S. K., Sanmartin M. J., Das D., Dalton Trans., 2013, 42, 16387—16395
[8]	Kumar A., Singh A. K., Gupta T., Analyst,2013, 138, 3356—3359
[9]	Orłowska M., Kłonkowski A. M., Jezierska J., Ryl J., Sensors and Actuators B,2013, 186, 396—406
[10]	Du J., Yin S., Jiang L., Ma B., Chen X., Chem. Commun., 2013, 49, 4196—4198
[11]	Tong D., Duan H., Zhuang H., Cao J., Wei Z., Lin Y., RSC Adv., 2014, 4, 5363—5366
[12]	Zhao X. Y., Chinese Journal of Practical Stomatology, 2010, 3, 449—451
	(赵信义. 中国实用口腔科杂志, 2010, 3, 449—451)
[13]	Yang J., Huang Z. J., Hou S. H., Ouyang J. M., Spectroscopy and Spectral Analysis,2011, 31, 168—182
	(杨锦, 黄志杰, 侯善华, 欧阳健明. 光谱学与光谱分析, 2011, 31, 168—182)
[14]	Kim H. N., Ren W. X., Kim J. S., Yoon J., Chem. Soc. Rev., 2012, 41, 3210—3244
[15]	Zhang G. Q., Xue M., Huo F. J., Yin C. X., Yan X. X., Jin S., Chem. J. Chinese Universities,2013, 34(9), 2090—2096
	(张改清, 薛玫, 霍方俊, 阴彩霞, 颜叙秀, 金硕. 高等学校化学学报, 2013, 34(9), 2090—2096)
[16]	Li J. B., Han C., Zhang S. J., Guo J. W., Zhou H. Y., Chem. J. Chinese Universities,2013, 34(10), 2303—2307
	(李军波, 韩晨, 张世杰, 郭进武, 周惠云. 高等学校化学学报, 2013, 34(10), 2303—2307)
[17]	Goswami S., Aich K., Das S., Das A. K., Sarkar D., Panja S., Mondal T. K., Mukhopadhyay S., Chem. Commun., 2013, 49, 10739—10741
[18]	Li W., Yang Y., Chen J., Zhang Q., Wang Y., Wang F., Yu C., Biosensors and Bioelectronics,2014, 53, 245—249
[19]	Santos-Figueroa L. E., Moragues M. E., Climent E., Agostini A., Martinez-Manez R., Sancenon F., Chem. Soc. Rev., 2013, 42, 3489—3613
[20]	Emami K. M., Wallace K. D., Hossain M. A., Tetrahedron Lett., 2014, 55, 438—440
[21]	Chen J., Liu C., Zhang J., Ding W., Zhou M., Wu F., Chem. Commun., 2013, 49, 10814—10186
[22]	Li G., Wu Y., Gao J., Li J., Zhao Y., Zhang Q., Chem. Asian J., 2013, 8, 1574—1578
[23]	Tong D., Duan H., Wang J., Yang Z., Lin Y., Sensors and Actuators B,2014, 195, 80—84
[24]	Jao C. W., Lin W. C., Wu Y. T., Wu P. L., J. Nat. Prod., 2008, 71, 1275—1279
[25]	Yu S. T., Chern J. W., Chen T. M., Chiu Y. F., Chen H. T., Chen Y. H., Acta Pharmacologica Sinica,2010, 31, 259—264
[26]	Krivogorsky B., Nelson A. C., Douglas K. A., Grundt P., Bioorg. Med. Chem. Lett., 2013, 23, 1032—1035
[27]	Wang Q., Xie Y., Ding Y., Li X., Zhu W., Chem. Commun., 2010, 46, 3669—3671