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Regioselective synthesis of a series of 1,4-disubstituted of naphthoxymethyl-N-alkyl naphthalimide-1,2,3-triazoles employing click reaction is presented. Highly selective and efficient copper(I)-catalysed 1,3-dipolar cyclo addition between 1-naphthylpropargylic ether and azido alkyl naphthalimides yielded the title compounds in 74% to 94%. The structure of all the new 1,2,3-triazoles was characterized by 1 HNMR, 13 C NMR, IR and Mass. The electronic absorption and emission studies revealed that the light absorbing and emitting chromophore is the naphthoxy moiety. There is no extensive delocalization of aromatic π-electrons in the active chromophore which exhibited lower quantum yields and lower Stokes shifts.

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Triarylborane substituted naphthalimide 3 was designed and synthesized by the Sonogashira cross-coupling reaction. The electronic absorption and emission spectra of the triarylborane naphthalimide 3 show red shifted absorption and emission as compared to 4-bromonaphthalimide 2. The sensing behaviour of 3 was studied for different anions. The triarylborane naphthalimide 3 selectively detects F(-) and CN(-) ions in the presence of Cl(-), Br(-), I(-) and NO2(-) ions. The effect of F(-) and CN(-) ions on the structure of 3 was studied by performing DFT calculations. The theoretical calculations show good agreement with the experimental results. The detection limits for F(-) and CN(-) were found to be 2.01 × 10(-10) M and 3.94 × 10(-10) M respectively.