Synthesis and Properties of Novel Fluorescence Probe Based on 1,8-Naphthalimide for Detection of Hydrogen Sulfide

Abstract

Two fluorescence-enhanced probes, 4-(2,4-dinitrophenoxy)-N-(2-hydroxyethyl)-1,8-naphthalimide(NTE-1) and 4-(2,4-dinitrophenoxy)-N-(4-(2,4-dinitrophenoxy)phenyl)-1,8-naphthalimide(NTE-2), have been designed and synthesized for detection of H₂S. 4-Hydroxy-1,8-naphthalimide as fluorophore in combination with 2,4-dinitrophenyl ether as H₂S response site constructed the fluorescence probes. The consequences showed that both NTE-1 and NTE-2 displayed large red-shift(excess 100 nm) in absorption spectra and more than 30-fold fluorescence enhancement in response to H₂S. Moreover, the dual site probe, NTE-2, displayed wider linear range between fluorescence intensity and concentration of H₂S(0—40 μmol/L) compared with single site probe, which can be applied to quantitative detection of high concentration of H₂S. The photoinduced electron transfer(PET) response mechanism of probe was further studied by analyzing the distributions of molecular orbital. Importantly, the probes have potential practical applications in detection of H₂S.

Keywords

2,4-Dinitrophenyl ether / Dual site / Gaussian / Photoinduced electron transfer

References

[1] Kashfi K., Olson K. R. Biochem. Pharm., 2013, 85(5): 689.

[2] Nagy P., Winterboum C. C. Chem. Res. Toxicol., 2010, 23(10): 1541.

[3] Hughes M. N., Centelles M. N., Moore K. P. Free. Radical. Bio. Med., 2009, 47(10): 1346.

[4] Zhang H., Jiao H., Jiang C. X., Wang S. H., Wei Z. J., Luo J. P., Jones R. L. Acta Physiol. Plant, 2010, 32(5): 849.

[5] Ma H., Cheng X., Li G. Q., Chen S. H., Quan Z. L., Zhao S. Y., Niu L. Corros. Sci., 2000, 42(10): 1669.

[6] Furne J., Saeed A., Levitt M. D. J. Physiol., 2008, 295(5): 1479.

[7] Tang T., Jiang G. F. New J. Chem., 2017, 41(14): 6769.

[8] Chen L. Y., Wu D., Lim C. S., Kim D., Nam S. J., Lee W., Kim G., Kim H. M., Yoon J. Chem. Commun., 2017, 53(35): 4791.

[9] Lawrence N. S., Davis J., Jiang J., Jones T. G. J., Davis S. N., Compton R. G. Electroanalysis, 2000, 25(4): 661.

[10] Li W. H., Sun W., Yu X. Q., Du L. P., Li M. Y. J. Fluoresc., 2013, 23(1): 181.

[11] Li W., Zhu Z. T., Li Y. Y., Yi L., Xi Z. Chem. Commun., 2015, 51(52): 10463.

[12] Liu H. Y., Zhao M., Qiao Q. L., Lang H. J., Xu J. Z., Xu Z. C. Chin. Chem. Lett., 2014, 25(7): 1060.

[13] Fu Y. J., Yao H. W., Zhu X. Y., Guo X. F., Wang H. Anal. Chim. Acta, 2017, 994: 1.

[14] Zhang J., Peng F. F., Dong X. C., Zhao W. L. Chem. Lett., 2015, 44(11): 1524.

[15] Fan F. L., Jing J. Q., Chen X. M. Chin. J. Org. Chem., 2014, 34(10): 2178.

[16] Gao B. Z., Cui L. X., Pan Y., Xue M. J., Zhu B. Y., Zhang G. M., Zhang C. H., Shuang S. M., Dong C. Spectrochim. Acta A, 2017, 173: 457.

[17] Liu T. Y., Zhang X. F., Qiao Q. L., Zou C. Y., Cui J. N., Xu Z. C. Dyes Pigm., 2013, 99(3): 537.

[18] Yuan L., Zuo Q. P. Sens. Actuat B: Chem., 2014, 196: 151.

[19] Liu X. L., Du X. J., Dai C. G., Qin H.S. J. Org. Chem., 2014, 79(20): 9481.

[20] And N. N., Ishitani A., Dixon D. A., Uda T. J. Phys. Chem. A., 2001, 105(20): 4953.

[21] Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J. A., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Keith T., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas O., Foresman J. B., Ortiz J.V., Cioslowski J., Fox D. J. GAUSSIAN 09, Revision C.01, Gaussian Inc., 2010.

[22] Stephens P. J., Devilin F. G., Chabalowski C. F., Frisch M. J. J. Phys. Chem., 1994, 98: 11623.

[23] Lu T., Chen F. W. J. Comput. Chem., 2012, 33(5): 580.

[24] Takeshi Y., David P. T., Nicholas C. H. Chem. Phys. Lett., 2004, 393(1): 51.

[25] Yu L. I., Jiang L. Chem. Res. Chinese Universities, 2014, 30(6): 997.

[26] Liu T. Y., Xu Z. C., Spring D. R., Cui J. N. Org. Lett., 2013, 15(9): 2310.

[27] Chinapang P., Ruangpornvisuti V., Sukwattanasinitt M., Rashatasakhon P. Dyes Pigm., 2015, 112: 236.

[28] Montoya L.A., Pluth M. D. Chem. Commun., 2012, 48(39): 4767.

[29] Bamesberger A., Schwartz C., Song Q., Han W. W., Wang Z., Cao H. S. New J. Chem., 2014, 38(3): 884.

[30] Fleming C. L., Nalder T. D., Doeven E. H., Barrow C. J., Pfeffer F. M., Ashton T. D. Dyes Pigm., 2016, 126: 128.

[31] Bae S. K., Heo C. H., Choi D. J., Sen D., Joe E. H., Cho B. C., Kim H. M. J. Am. Chem. Soc., 2013, 135: 9915.

[32] Liu X. L., Du X. J., Dai C. G., Song Q. H. J. Org. Chem., 2014, 79(20): 9481.

[33] Feng W. Q., Mao Z. Q., Liu L. Z., Liu Z. H. Talanta, 2017, 167: 134.

[34] Das S. K., Lim C. S., Yang S. Y., Han J. H., Cho B. R. Chem. Commun., 2012, 48(67): 8395.

[35] Liu K. R., Liu C., Shang H. M., Ren M. G., Lin W. Y. Sens. Actuat. B: Chem., 2018, 256: 342.

[36] Zheng K. B., Lin W. Y., Tan L., Cheng D. Anal. Chim. Acta, 2015, 853: 548.

[37] Zhou Y., Wang Y. K., Wang X. F., Zhang Y. J., Wang C. K. Chin. Phys. B., 2017, 26(8): 123.

[38] Liu X. J., Lin T., Gao S. W., Ma R., Zhang J. Y., Cai X. C., Yang L., Teng F. Acta Phys.-Chem. Sin., 2012, 28(6): 1337.

[39] Zhang Y. J., Yang W. J., Wang C. K. Chem. Phys., 2016, 468: 37.