Molecular Full-adder and Full-subtractor Logic Circuit Based on Fluorescein Derivatives†

doi:10.7503/cjcu20140668

Abstract

Abstract:

Over the past decade, there has been significant progress in the development of molecular compu-ter, which has inspired scientists to construct appropriate molecular systems that could integrate simple logic gates into combinatorial circuits. In this work, a novel fluorescein-based QHF⁺ with five-state molecular switch was synthesized. The conversion of the five states of QHF⁺ was observed by UV-visible absorption spectra under various pH values in CH₃CH₂OH/H₂O(volume ratio 1∶1). Spectral responses with the use of chemical inputs in the form of H⁺ and OH^- revealed that QHF could function as a combinatorial logic circuit(XOR gate and INHIBIT gate, AND gate and XOR gate). Absorbance change at 424 and 490 nm or transmittance change at 424 nm, was monitored as output signals with threshold value of A=0.209(or T=61.8%). When absorbance intensity or transmittance percentage was more than the threshold value, the output signal was 1. Otherwise, the output value was 0. In conclusion, a full-subtractor was achieved by setting the initial state to QHF⁰ with outputs at 424 and 490 nm in the absorption mode, while a molecular full-adder was provided by setting the initial state to QHF⁺ and observing both absorbance at 490 nm and transmittance at 424 nm.

Key words: Fluorescein, Molecular logic circuit, UV-vis absorption spectrum, Full-subtractor, Full-adder

CLC Number:

O626

TrendMD:

TIAN Tao, LIU Chang, HE Song, ZENG Xianshun. Molecular Full-adder and Full-subtractor Logic Circuit Based on Fluorescein Derivatives^†[J]. Chem. J. Chinese Universities, 2015, 36(2): 260.

Figures/Tables 7

Scheme 1 Synthetic routes for fluorescein aldehyde 1 and compounds QHF+

Scheme 2 Schematic representation of interconversion of QHF+ among five ionization states in the presence of acid and base

Fig.1 UV-Vis absorption spectra for each of the ionization forms of QHF+(1×10-5 mol/L) in a ethanol/water(volume ratio 1∶1)

Table 1 Truth table of the three states QHF+, QHF0 and QHF- under a various of pH with the function*

Input		Output		Half-Subtractor(B/D)
$X H +$	$Y O H -$	INH_490nm Borrow	XOR_424nm Difference	X-Y 490/424 nm
0	0	0(low, 0.162)	0(low, 0.205)	00
1	0	0(low, 0.069)	1(high, 0.228)	01
0	1	1(high, 0.347)	1(high, 0.229)	11
1	1	0(low, 0.162)	0(low, 0.205)	00

Table 1 Truth table of the three states QHF+, QHF0 and QHF- under a various of pH with the function*

Input		Output		Half-Subtractor(B/D)
$X H +$	$Y O H -$	INH_490nm Borrow	XOR_424nm Difference	X-Y 490/424 nm
0	0	0(low, 0.162)	0(low, 0.205)	00
1	0	0(low, 0.069)	1(high, 0.228)	01
0	1	1(high, 0.347)	1(high, 0.229)	11
1	1	0(low, 0.162)	0(low, 0.205)	00

Table 2 Truth table of full-subtractor circuit*

Line	Input			Output		Line	Input			Output
Line	X	Y		B_in	Borrow out 490 nm	Difference 424 nm	X	Y	B_in	Borrow out 490 nm	Difference 424 nm
a	0	0	0	0	0	e	0	0	OH^-	1	1
b	0	OH^-	0	1	1	f	0	OH^-	OH^-	1	0
c	H⁺	0	0	0	1	g	H⁺	0	OH^-	0	0
d	H⁺	OH^-	0	0	0	h	H⁺	OH^-	OH^-	1	1

Table 3 Truth table of a new type half-adder device*

Input		Output
$X O H -$	$Y O H -$	AND(A) 490 nm	XOR[T(%)] 424 nm	NXOR(A) 424 nm
0	0	0(low, 0.07)	0(low, 59.8)	1(high, 0.223)
0	1	0(low, 0.204)	1(high, 68.9)	0(low, 0.162)
1	0	0(low, 0.204)	1(high, 68.9)	0(low, 0.162)
1	1	1(high, 0.335)	0(low, 59.7)	1(high, 0.224)

Table 3 Truth table of a new type half-adder device*

Input		Output
$X O H -$	$Y O H -$	AND(A) 490 nm	XOR[T(%)] 424 nm	NXOR(A) 424 nm
0	0	0(low, 0.07)	0(low, 59.8)	1(high, 0.223)
0	1	0(low, 0.204)	1(high, 68.9)	0(low, 0.162)
1	0	0(low, 0.204)	1(high, 68.9)	0(low, 0.162)
1	1	1(high, 0.335)	0(low, 59.7)	1(high, 0.224)

Table 4 Truth table of the full-adder circuit*

Line	Input			Output		Line	Input			Output
Line	X	Y		C_in	Carry out 490 nm(A)	Sum 424 nm(T)	X	Y	C_in	Carry out 490 nm(A)	Sum 424 nm(T)
a	0	0	0	0	0	e	0	0	OH^-	0	1
b	0	OH^-	0	0	1	f	0	OH^-	OH^-	1	0
c	OH^-	0	0	0	1	g	OH^-	0	OH^-	1	0
d	OH^-	OH^-	0	1	0	h	OH^-	OH^-	OH^-	1	1

References 40

[1]	Guliyev R., Ozturk S., Kostereli Z., Akkaya E. U., Angew. Chem. Int. Ed., 2011, 50(42), 9826—9831
[2]	Cao J., Ma X., Min M., Cao T., Wu S., Tian H., Chem. Commun., 2014, 50, 3224—3226
[3]	Orbach R., Remacle F., Levine R. D., Willner I., Chem. Science, 2014, 5(49), 1074—1081
[4]	Andréasson J., Pischel U., Chem. Soc. Rev., 2010, 39(9), 174—188
[5]	Szaciłowski K., Chem. Rev., 2008, 108(9), 3481—3548
[6]	Elbaz J., Lioubashevski O., Wang F., Remacle F., Levine R. D., Willner I., Nat. Nanotechnol., 2010, 5(9), 417—423
[7]	Nolan E. M., Lippard S., J. Chem. Rev., 2008, 108, 3443—3480
[8]	Tian H., Angew. Chem. Int. Ed., 2010, 49(28), 4710—4712
[9]	De Ruiter G., Motiei L., Choudhury J., Oded N., Boom M. E., Angew. Chem. Int. Ed., 2010, 49(28), 4780—4783
[10]	De Silva A. P., Gunaratne H. Q. N., McCoy C. P., Nature, 1993, 364, 42—44
[11]	Collier C. P., Wong E. W., Belohradsky M., Raymo F. M., Stoddart J. F., Kuekes P. J., Williams R. S., J. R. Science, 1999, 285, 391—394
[12]	Credi A., Balzani V., Langford S. J., Stoddart J. F., J. Am. Chem. Soc., 1997, 119(11), 2679—2681
[13]	Asakawa M., Ashton P. R., Balzani V., Credi A., Mattersteig G., Matthews O. A., Montalti M., Spencer N., Stoddart J. F., Venturi M., Chem. Eur. J., 1997, 3(12), 1992—1996
[14]	Baytekin H. T., Akkaya E. U., Org. Lett., 2000, 2(12), 1725—1727
[15]	De Silva A. P., Dixon I. M., Gunaratne H. Q. N., Gunnlaugsson.T., Maxwell P. R. S., Rice T. E., J. Am. Chem. Soc., 1999, 121(6), 1393—1394
[16]	Liu Y., Jiang W., Zhang H. Y., J. Phys. Chem. B, 2006, 110(29), 14231—14235
[17]	Liu D. B., Chen W. W., Sun K., Deng K., Zhang W., Jiang X. Y., Angew. Chem. Int. Ed., 2011, 50(32), 4103—4107
[18]	Langford S. J., Yann T., J. Am. Chem. Soc., 2003, 125(37), 11198—11199
[19]	Margulies D., Melman G., Felder C. E., Arad-Yellin R., Shanzer A., J. Am. Chem. Soc., 2004, 126(47), 15400—15401
[20]	Andréasson J., Kodis G., Terazono Y., Liddell P. A., Bandyopadhyay S., Mitchell R. H., Moore A. L., Gust D., J. Am. Chem. Soc., 2004, 126(49), 15926—15927
[21]	Guo X. F., Zhang D. Q., Zhang G. X., Zhu D. B., J. Phys. Chem. B, 2004, 108(32), 11942—11945
[22]	Wang H. G., Liu D. H., Zhang C. Q., Li Y. X., Yang Q. B., Du J. S., Chem. J. Chinese Universities, 2012, 33(5), 1074—1077
	(王恒国, 刘大海, 张朝群, 李耀先, 杨清彪, 杜建时. 高等学校化学学报, 2012, 33(5), 1074—1077)
[23]	Su W., Yang B., Chem. Res. Chinese Universities, 2013, 29(4), 657—662
[24]	He S., Liu Q., Li Y., Wei F., Cai S., Lu Y., Zeng X., Chem. Res. Chinese Universities, 2014, 30(1), 32—36
[25]	Liu C., Huang S., Lu Y., He S., Zhao L., Zeng X., RSC Adv., 2014, 4, 16109—16114
[26]	Cai S., Lu Y., He S., Wei F., Zhao L., Zeng X., Chem. Commun., 2013, 49, 822—824
[27]	Wei F., Lu Y., He S., Zhao L., Zeng X., Anal. Methods, 2012, 4, 616—618
[28]	Chang L., Liu C., He S., Lu Y., Zhang S., Zhao L., Zeng X., Sen. Actuators B, 2014, 202, 483—488
[29]	Liu Q., Liu C., He S., Lu Y., Zhao L., Zeng X., RSC Adv., 2014, 4, 14361—14364
[30]	Chang J., Lu Y., He S., Liu C., Zhao L., Zeng X., Chem. Commun., 2013, 49, 6259—6261
[31]	Wang Q., Liu C., Lu Y., He S., Liu C., Zhao L., Zeng X., Dyes Pigments, 2013, 99, 733—739
[32]	Li Y., He S., Lu Y., Zhao L., Zeng X., Dyes Pigments, 2013, 96, 424—429
[33]	Li Y. Y., Lu Y., He S., Zeng X. S., Chem. J. Chinese Universities, 2011, 32(9), 2123—2127
	(李园园, 陆燕, 何松, 曾宪顺. 高等学校化学学报, 2011, 32(9), 2123—2127)
[34]	Sun W., Zheng Y. R., Xu C. H., Fang C. J., Yan C. H., J. Phys. Chem. C, 2007, 111(31), 11706—11711
[35]	Suresh M., Joes D.A., Das A., Org. Lett., 2007, 9(3), 441—444
[36]	Margulies D., Melman G., Shanzer A., Nat. Mater., 2005, 4, 768—770
[37]	De Silva A.P., Rice T. E.,Chem. Commun., 1999, 163—164
[38]	Liu C., Lu Y., He S., Zeng X. S., J. Mater. Chem. C, 2013, 1, 4770—4778
[39]	Wang W., Rusin O., Xu X., Kim K. K., Escobedo J. O., Fakayode S. O., Fletcher K. A., Lowry M., Schowalter C. M., Lawrence C. M., Fronczek F. R., Warner I. M., Strongin R. M., J. Am. Chem. Soc., 2005, 127(45), 15949—15958
[40]	Margulies D., Melman G., Shanzer A., J. Am. Chem. Soc., 2006, 128(14), 4865—4871
	(Ed.: P, H, W, K)

Related Articles 15

[1]	LIANG Zupei, SU Feifei, GUO Rong, TANG Yuyao, JIN Shuo, YU Zihuan, LI Jian, MA Shulan. Photoluminescence Property of Layered Double Hydroxide Composite with Fluorescein and Detection Towards F $e 3 + †$ [J]. Chem. J. Chinese Universities, 2019, 40(7): 1352.
[2]	LIU Dahai, ZHANG Xueyan, FENG Yusha, DU Xianlong, XUE Longqi, DU Jianshi, ZHANG Guirong, YANG Qingbiao, LI Yaoxian. Synthesis of Novel Fluorescein-Thiospirolactams Hg²⁺ Fluorescent Probes and Its Application in vivo^† [J]. Chem. J. Chinese Universities, 2018, 39(7): 1412.
[3]	ZHANG Tao, TANG Yongjia, XU Liang, LIU Keliang. Synthesis of a New Cyanoacrylate Monomer and Its Application in Fluorescence Imaging in vivo^† [J]. Chem. J. Chinese Universities, 2016, 37(6): 1168.
[4]	WANG Heng-Guo, LIU Da-Hai, ZHANG Chao-Qun, LI Yao-Xian, YANG Qing-Biao, DU Jian-Shi. Preparation and Characterization of Fluorescent Nanofiber Based on Fluorescein [J]. Chem. J. Chinese Universities, 2012, 33(05): 1074.
[5]	GAN Xiao-Juan, LIU Shao-Pu, LIU Zhong-Fang, HU Xiao-Li. Fluorescence Quenching Method for the Determination of Carbazochromum with Halide Fluorescein Dyes [J]. Chem. J. Chinese Universities, 2012, 33(04): 683.
[6]	ZHANG Hui-Zhong, NIE Fei, Lü Jiu-Ru. Post-chemluminescence Reaction of Some Nitrogenous Organic Compounds in the N-Chlorosuccinimide-dichlorofluorescein System [J]. Chem. J. Chinese Universities, 2010, 31(1): 51.
[7]	LIANG Chong-Yang¹, XU Wei-Qing², CAO Yan-Xin², LIU Li-Xia³, ZHANG Shu-Qin¹, LIU Zhi-Yi¹, LI Hong-Rui¹, LI Bai-Zhi¹, SUN Fei^1* . Dynamic Observation of Cellular Localization of Fluorescein Isothiocyanate Labeled Recombinant Ganoderma Lucidum Immunoregulatory Protein(rLz-8) in NB4 APL Cell [J]. Chem. J. Chinese Universities, 2009, 30(3): 489.
[8]	LIN Bing, CAI Ming , LI Wei*. PCM-TDDFT Study of the UV-Vis Spectra of Photochromic Spirooxazine and Spiropyran Compound [J]. Chem. J. Chinese Universities, 2009, 30(11(1)): 96.
[9]	HAN Jie, LI Jian-Li, HE Huai-Zhen, WU Xiang-Long, SHI Zhen^*. Design, Synthesis and Characterization of Novel Fluorescein-based Calcium Fluorescent Probe Fluo-Cl [J]. Chem. J. Chinese Universities, 2008, 29(10): 2003.
[10]	GUAN Xiao-Lin, LIU Xing-Yu, SU Zhi-Xing*. Synthesis and Luminescent Property of a Novel Fluorescent Dual Sensitive Chitosan [J]. Chem. J. Chinese Universities, 2006, 27(6): 1145.
[11]	JIANG Zhi-Liang, LIU Shao-Pu, WANG Li-Sheng, QIN Ai-Miao, LIANG Hong . Spectroscopic Characteristic of the Gold Nanoparticle-fluorescein System [J]. Chem. J. Chinese Universities, 2003, 24(7): 1201.
[12]	ZHANG Sheng-Mao, ZHANG Zhi-Jun, DANG Hong-Xin, LIU Wei-Min, XUE Qun-Ji . Preparation and Characterization of Orderly Alternating TiO₂/CTAB Multilayer Film [J]. Chem. J. Chinese Universities, 2003, 24(6): 1136.
[13]	ZHANG Hai-Ping, ZHOU Ya-Lin, ZHANG Man-Hua, SHEN Tao, LI Yu-Liang, ZHU Dao-Ben . Photo-induced Intramolecular Electron Transfer of Fluorescein-anthraquinone-methyl Ester and Detection of Its Charge-separated State [J]. Chem. J. Chinese Universities, 2003, 24(3): 492.
[14]	DUAN Jing-Hua, WANG Ke-Min, TAN Wei-Hong, HE Xiao-Xiao, HE Chun-Mei, LIU Bin, LI Du, HUANG Shan-Sheng, YANG Xiao-Hai, MO Yuan-Yao. A Study of a Novel Organic Fluorescent Core-shell Nanoparticle [J]. Chem. J. Chinese Universities, 2003, 24(2): 255.
[15]	WAGN Feng-Bin, ZHENG Jun-Wei, LI Xiao-Wei, JI Yuan, GAO Ying, XING Wei, LU Tian-Hong. Electrochemical Study of Microperoxidase-11 Immobilized on the Surface of a Poly-L-lysine Modified Gold Electrode [J]. Chem. J. Chinese Universities, 2003, 24(12): 2268.