American Journal of Sensor Technology
ISSN (Print): 2373-3454 ISSN (Online): 2373-3462 Website: Editor-in-chief: Vyacheslav Tuzlukov
Open Access
Journal Browser
American Journal of Sensor Technology. 2017, 4(1), 1-9
DOI: 10.12691/ajst-4-1-1
Open AccessArticle

N,N’-Diphenyldecanediamide: A Fluoride Ion Sensitive and Selective Amide

Meenakshi Thakran1, Anek pal Gupta1 and Neeru Dabas1,

1Amity School of Applied Sciences, Amity University Haryana, Panchgaon, Manesar, Gurgaon, Haryana, India

Pub. Date: March 02, 2017

Cite this paper:
Meenakshi Thakran, Anek pal Gupta and Neeru Dabas. N,N’-Diphenyldecanediamide: A Fluoride Ion Sensitive and Selective Amide. American Journal of Sensor Technology. 2017; 4(1):1-9. doi: 10.12691/ajst-4-1-1


A fluoride ion (F-) sensitive organic ligand N, N’-Diphenyldecanediamide (L1), has been synthesized by the reaction of sebacoyl chloride with aniline in presence of triethylamine at room temperature. Spectroscopic investigation revealed F- interacts strongly with L1 in comparison to other competitive anions (Cl-, Br- and NO3-) and as a consequence induces deprotonation in the NH fragment of L1. Different spectroscopic techniques such as 1H NMR, UV-Vis and fluorescence emission spectroscopy supports the fast and distinct response behavior of N, N’-substituted polymethylene diamide towards F-.

fluoride responsive selective flexible polymethylene diamide

Creative CommonsThis work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit


[1]  Hirsch, B. E., McDonald, K. P., Qiao, B., Flood, A. H., Tait, S. L. , “Selective Anion Induced Crystal Switching and Binding in Surface Monolayers Modulated by Electric Fields from Scanning Probes,” ACS Nano, 8 (10), 10858-10869, September 2014.
[2]  Gale, P. A., “Structural and Molecular Recognition Studies with Acyclic Anion Receptors,” Acc. Chem. Res. 39 (7), 465-475, May 2006.
[3]  Gladwin, M. T. , Schechter, A. N. , Kim-Shapiro, D. B. , Patel, R. P. , Hogg, N. , Shiva,S., Cannon, R. O., Kelm, M., Wink, D. A., Espey, M. G. , Oldfield, E. H. , Pluta, R. M. , Freeman, B. A. , Lancaster, J. R. , Feelisch, Jr, M. , Lundberg, J. O. , “The emerging biology of the nitrite ion,” Nature Chem. Bio. 1 (6), 308-314, November 2005.
[4]  Jentsch, T. J., Stein, V., Weinreich, F., Zdebik, A. A., “Molecular Structure and Physiological Function of Chloride Channels,” Physiol Rev. 82 (2), 503-568, April 2002.
[5]  Choi, A. L., Sun, G., Zhang, Y., Grandjean, P., “Developmental fluoride neurotoxicity: A systematic review and meta-analysis,” Environ. Health Perspect. 120 (10), 1362-1368, October 2012.
[6]  Phipps, K., “Fluoride and Bone Health,” Journal of Public Health Dent. 55 (1), 53-56, 1995.
[7]  Everett, E.T., “Fluoride’s Effects on the Formation of Teeth and Bones, and the Influence of Genetics,” J. Dent. Res. 90 (5), 552-560, May 2011.
[8]  Ludlow, M., Luxton, G., Mathew, T., “Effects of fluoridation of community water supplies for people with chronic kidney disease,” Nephrol. Dial. Transplant. 22, 2763-2767, July 2007.
[9]  Greenwood, D. A., “Fluoride Intoxication,” Physiological Rev. 20 (4), 582-616, October 1940.
[10]  Islam, Md. E.; Julkarnain, Md.; Hossain,J.; Ismail,A. B. Md.; Rahman, Md. H. “Investigation on LaF3 impregnated porous silicon heterostructur as potentiometric sensor for fluoride ion in aqueous medium,” Am. J. Sensor Technol. 1 (1), 1-4, October 2013.
[11]  Yuan, M.S., Wang, Q., Wang, W., Wang, D.E., Wang, J., Wang, J., “Truxenecored p-expanded triarylborane dyes as single- and two-photon fluorescent probes for fluoride,” Analyst. 139 (6), 1541-1549, March 2014.
[12]  Cai, J., Sessler, J. L., “Neutral CH and cationic CH donor groups as anion receptors,” Chem. Soc. Rev. 43, 6198-6213, May 2014.
[13]  Ghosh, D., Rhodes, S., Hawkins, K., Winder, D., Atkinson, A., Ming, W., Padgett, C., Orvis, J., Aiken, K., Landge, S., “A simple and effective 1,2,3-triazole based “turn on” fluorescence sensor for the detection of anions ,” New J. Chem. 39 (1), 295-303, October 2015.
[14]  Basaran, I., Khansari, M.E., Pramanik, A., Wong, B. M., Hossain, M. A. “An exclusive fluoride receptor: Fluoride-induced proton transfer to a quinoline-based thiourea,” Tetrahedron Lett. 55 (8), 1467-1470, February 2014.
[15]  Jun, E. J., Xu, Z., Lee, M., Yoon, J., “A ratiometric fluorescent probe for fluoride ions with a tridentate receptor of boronic acid and imidazolium,” Tetrahedron Lett. 54 (22), 2755-2758, May 2013.
[16]  Chahar, M., Pandey, P.S., “Design of steroid-based imidazolium receptors for fluoride ion recognition,” Tetrahedron, 64 (27), 6488-6493, June 2008.
[17]  Mohapatra, S., Sahu, S., Nayak, S., Ghosh, S.K., “Design of Fe3O4@SiO2@Carbon Quantum Dot Based Nanostructure for Fluorescence Sensing, Magnetic Separation, and Live Cell Imaging of Fluoride Ion,” Langmuir, 31 (29), 8111-8120, June 2015.
[18]  Liu, T., Nonat, A., Beyler, M., Regueiro-Figueroa, M., Nono, K. N., Jeannin, O., Camerel, F., Debaene,F., Cianferani-Sanglier, S., Tripier, R., Platas-Iglesias, C., Charbonniere, L. J., “Supramolecular Luminescent Lanthanide Dimers for Fluoride Sequestering and Sensing,” Angew. Chem. 126 (28), 7387-7391, July 2014.
[19]  Kang, S.O., Llinares, J. M., Powell, D., VanderVelde, D., Bowman-James, K., “New Polyamide Cryptand for Anion Binding,” J. Am. Chem. Soc. 125 (34), 10152-10153, July 2003.
[20]  Dorazco-Gonzalez, A., Hopfl, H., Medrano, F., Yatsimirsky, A.K., “Recognition of Anions and Neutral Guests by Dicationic Pyridine-2,6-dicarboxamide Receptors,” J. Org.Chem. 75(7), 2259-2273, March 2010.
[21]  Korendovych, I. V. , Cho, M., Butler, P. L., Staples, R. J., Rybak-Akimova, E. V., “Anion Binding to Monotopic and Ditopic Macrocyclic Amides,” Org. Lett. 8 (15), 3171-3174, June 2006.
[22]  Zhang, S., Palkar, A., Echegoyen, L., “Selective Anion Sensing Based on Tetra-amide Calix[6]arene Derivatives in Solution and Immobilized on Gold Surfaces via Self Assembled Monolayers,” Langmuir 22(25), 10732-10738, December 2006.
[23]  Dutta, R., Ghosh, P., “Encapsulation of Fluoride/Chloride in the C3v-Symmetric Cleft of a Pentafluorophenyl-Functionalized Cyanuric Acid Platform Based Tripodal Amide: Solid and Solution-State Anion-Binding Studies,” Eur. J. Inorg. Chem., 2012(21), 3456-3462, July 2012.
[24]  Bisson, A.P., Lynch, V. M., Monahan, M. K. C., Anslyn, E. V., “Recognition of Anions through NH π Hydrogen Bonds in a Bicyclic Cyclophane-Selectivity for Nitrate,” Angew. Chem. Int. Ed. 36 (21), 2340-2342, November 1997.
[25]  Li, J., Xu, X., Shao, X., Li, Z., “A novel colorimetric fluoride sensor based on a semirigid chromophore controlled by hydrogen bonding,” Luminescence 30(8), 1285-1289, December 2015.
[26]  Kim, Y., Song J. H. , Lee, W. R. , Phang, W. J. , Lim, K. S. , Hong CS. , “Reversible Structural Flexibility and Sensing Properties of a Zn(II) Metal-Organic Framework: Phase Transformation between Interpenetrating 3D Net and 2D Sheet.” Cryst. Growth Des, 14(4), 1933-1937, February 2014.
[27]  Steiner,T., “The Hydrogen Bond in the Solid State,” Angew. Chem. Int. Ed. 41 (1), 48-76, January 2002.
[28]  Boiocchi, M., Boca, L. D., Gomez, D.E., Fabbrizzi, L., Licchelli, M., Monzani, E., “Nature of urea fluoride interaction: incipient and definitive proton transfer” J. Am. Chem. Soc. 126 (50), 16507-16514, November 2004.
[29]  Elmes, R.B.P., Turner,P., Jolliffe, K.A.,“Colorimetric and Luminescent Sensors for Chloride: Hydrogen Bonding vs Deprotonation,” Org. Lett. 15 (22), 5638-5641, October 2013.
[30]  Yang, Z., Zhang, K., Gong, F., Li,S., Chen, J., Ma, J.S., Sobenina, L.N., Mikhaleva, A. I. , Yang, G., Trofimov, B. A., “A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative,” Beilstein J. Org. Chem. 7, 46-52, January 2011.
[31]  Liu, B., Tian, H., “A ratiometric fluorescent chemosensor for fluoride ions based on a proton transfer signaling mechanism,” J. Mater. Chem. 15 (27-28), 2681-2686, May 2005.