| Two novel 1,8-naphthalimide derivatives were synthesized while 4-bromo-1,8-naphthalic anhydride was the raw material. They were namely tert-butoxycarbonyl-{N,N-bis{3,5-bis{2-(4-tert-butylphenyl)-5-[1,3,4]-oxadiazolyl}-styryl-1,8-naphathlimide}-ethylaminocarbonyleth yl}ethylamino}-1,8-naphthalimide (DON) and 4-piperidyl-9-ethylamino-{N,N-bis{3,5-bis {2-(4-tert-butylphenyl)-5-[1,3,4]-oxadiazolyl}-styryl-1,8-naphathlimide}-ethylaminocarbonyl ethyl}ethylamino}1,8-naphthalimide(DOPN). Besides, two fluorescent molecules deriving from combination of fluophores rhodamine and naphthalene imide, were prepared, named N,N’-rhodamine acyl ethylamino-4- pyridine vinyl-1,8-naphathlimide (2py-RB) and N,N’-rhodamine acyl ethylamino-4-{(tert-butylphenyl)-5-[1,3,4]-oxadiazolyI}-styryl-1,8-naphathlimide (Oxa-NtRB) respectively. And these products were characterized by 1HNMR, 13C NMR and HRMS techniques and their solids were characterized by melting point, FTIR,1 HNMR and MS. In this paper, the Aggregation induced emission charateristic of the four compounds were investigated. Moreover, when coming to probes for metal ions, the response behavious of DON to Sn2+ and DOPN to Cu2+were studied. And the reserches on the behavious of DON and DOPN, combinating with BSA, and imaging of the two fluorescence probe in living cell were conducetd. Additionally, the appropriate mechanisms on recognizing metal ions of DON and DOPN were talked about. On the other hand, the selective recognition for Hg2+ and Cr3+, behavious of response to H+ and living cell imaging of two luminescent molecules based on rhodamine-naphthalimide,2Py-RB and Oxa-NtRB were investigated. What’s more, mechanisms of recognition of metal ions and acid-base response were discussed in details in the contribution.1. Aggregation induced emission of naphthalimide compound DON and DOPN and naphthalimide-rhodamine derivative 2Py-RB and Oxa-NtRB were investigated, and the results indicated that the naphthalimide dendrimer molecules (DON and DOPN) exhibited obvious AIE effect. In solid states, both of the dyes emitted orange fluorescence and their maximum wavelengths were 566 and 561 nm, respectively. And in THF solution, they possessed blue emission. The two fluorophores can be dissolved in common organic solvents. When in the mixed solution of organic THF and water, their fluorescence intensities were weakened gradually with the increasing of water fraction. More intriguingly,2Py-RB and Oxa-NtRB possessed the characteristic phenonmenon of AIEE. In their aggragation, the two rhodamine-naphthalimide derivatives performed kermesinus emission and their maximum wavelengths were both at 608 nm. The two fluorescene probe were nearly colorless in pure ethanol solution while their luminescence intensities were enhanced increasingly with the water ratio increasing in the ethanol and water system.2. The behavious of selective metal ions recognition of naphthalimide dendrimer molecules (DON for Sn2+ and DOPN for Cu2+) were studied. It was observed that DON appeared to be a good selective probe for Sn2+with the limit of detection of 1.38×10-6 M, and its fluorescence intensity enhanced when combinated with Sn2+, while DOPN selectively associated with Cu2+ quenched the fluorescence emission with the limit of detection of 2.25×10-7 M. And proper mechanisms of recognition of metal ions were investigated concretely. Besides, bioapplications experiments of two dyes were conduceted. And the results demonstrated that DON and DOPN were responsed to biomolecules BSA, and their luminescence emission were quenched when interacting with BSA, and the quencher constants were 6.11×104 and 3.98×104 respectively. Finally, the HeLa cell imagings of two fluorephores were obtained.3. In addition, according to the experiments,2Py-RB and Oxa-NtRB based on rhodamine-naphthalimide can be well served as selective probes for Hg2+ and Cr3+. Based on the fitted curves,2Py-RB and Oxa-NtRB recognized Hg2+ and Cr3+ by means of ratio recognition, meanwhile, the two compounds based on rhodamine and naphthalimide can make a dual-channal recognizztion for Hg2+ and Cr3+ ions at 450 and 578 nm. Then the appropriate mechanisms of recognition to 2Py-RB and Oxa-NtRB for Hg2+ and Cr3+ were dissgussed. Furthermore, identification with proton and Hela cell imaing applications were also studied. |
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