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Surfactant Dependent pH Controlled “off-on”, “off-on-off” and “on-off” Fluorescent Switches Exhibited by N-Benzylidenenaphthalen-1-Amine

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Abstract

N-benzylidenenaphthalen-1-amine (L) acts as pH dependent “off-on”, “off-on-off” and “on-off” fluorescent switch in 1:1 (v/v) CH3CN:H2O depending on the presence of anionic sodiumdocdecyl sulphate (SDS), neutral triton X-100 (TX-100) and cationic cetyltrimethylammonium bromide (CTAB) surfactants respectively. DFT calculation shows the possibility of formation of L.H+ due to protonation at immine N and L.OH− due to introduction of OH− group at immine C. The relative stability of these two cationic and anionic species depends on the charge environment provided by surfactants. This influences the photoinduced electron transfer (PET) processes involved and results in different switch behaviour.

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References

  1. de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, Mc Coy CP, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515–1566

    Article  PubMed  Google Scholar 

  2. Szaciłowski K (2008) Digital information processing in molecular systems. Chem Rev 108:3481–3548

    Article  PubMed  Google Scholar 

  3. Amendola V, Fabbrizzi L, Mangano C, Miller H, Pallavicini P, Parotti A, Taglietti A (2002) Signal amplification by a fluorescent indicator of a pH-driven intramolecular translocation of a copper(II) ion. Angew Chem Int Ed 41:2553–2556

    Article  CAS  Google Scholar 

  4. Gunnlaugsson T, Lee TC, Parkesh R (2004) Highly selective fluorescent chemosensors for cadmium in water. Tetrahedron 60:11239–11249

    Article  CAS  Google Scholar 

  5. Shiraishi Y, Kohno Y, Hirai T (2005) Bis-azamacrocyclic anthracene as a fluorescent chemosensor for cations in aqueous solution. J Phys Chem B 109:19139–19147

    Article  CAS  PubMed  Google Scholar 

  6. Nishimura G, Shiraishi Y, Hirai T (2005) A fluorescent chemosensor for wide-range pH detection. Chem Commun 42:5313–5315

    Article  Google Scholar 

  7. Shiraishi Y, Tokitoh Y, Nishimura G, Hirai T (2005) A molecular switch with pH-controlled absolutely switchable dual-mode Fluorescence. Org Lett 7:2611

    Article  CAS  PubMed  Google Scholar 

  8. Shiraishi Y, Tokitoh Y, Hirai T (2006) pH and H2O driven triple-mode pyrene fluorescence. Org Lett 8:3841–3844

    Article  CAS  PubMed  Google Scholar 

  9. Pallavicini P, Amendola V, Massera C, Mundum E, Taglietti A (2002) ‘On–off–on’ fluorescent indicators of pH windows based on three separated components. Chem Commun 2452–2453

  10. Albelda MT, Bernardo MA, Diaz P, Garcia-Espan widetilde E, Melo JS, Pina F, Soriano C, Luis SV (2001) Polyamines containing naphthyl groups as pH-regulated molecular machines driven by light. Chem Commun 1520–1521

  11. de Silva SA, Amorelli B, Isidor DC, Loo KC, Crooker KE, Pena YE (2002) A fluorescent ‘off-on-off’ proton switch with an overriding ‘enable-disable’ sodium ion switch Chem Commun 1360–1361

  12. de Silva SA, Loo KC, Amorelli B, Pathirana SL, Nyakirang’ani M, Dharmasena M, Demarais S, Dorcley B, Pullay P, Salih YA (2005) A fluorescent “off–on–off” proton switch derived from natural products and further studies of first-generation fluorescent photoinduced electron transfer (PET) systems. J Mater Chem 15:2791–2795

    Article  Google Scholar 

  13. Singh P, Kumar S (2006) A unique ON–OFF–ON switch with two perturbations at two different concentrations of Ag+. Tetrahedron Lett 47:109–112

    Article  CAS  Google Scholar 

  14. Bandyopadhyay P, Ghosh AK (2009) pH-Controlled “off-on-off” switch based on Cu2+-mediated pyrene fluorescence in a PAA-SDS micelle aggregated supramolecular system. Phys Chem B 113:13462–13464

    Article  CAS  Google Scholar 

  15. Goswami P, Das DK (2011) Significant effect of surfactant micelles on pH dependent fluorescent off–on–off behavior of salicylaldehyde-2,4-dinitrophenylhydrazone. J Lumin 131:760–763

    Article  CAS  Google Scholar 

  16. Das DK, Dutta K (2014) pH dependent fluorescence switching in salicylideneaniline: ‘off–on–off’ operation controlled by surfactant micelles. J Lumin 145:454–458

    Article  CAS  Google Scholar 

  17. Kumar J, Sarma MJ, Phukan P, Das DK (2015) A new simple Schiff base fluorescence “on” sensor for Al3+ and its living cell imaging. Dalton Trans 44:4576–4581

    Article  CAS  PubMed  Google Scholar 

  18. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2013) Gaussian 09, Revision B.01. Gaussian, Inc, Wallingford

    Google Scholar 

  19. Becke AD (1993) Density‐functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652

    Article  CAS  Google Scholar 

  20. Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789

    Article  CAS  Google Scholar 

  21. Weiss K, Warren CH, Wettermark G (1971) Cis-Trans Isomerization about the carbon-nitrogen double bond. The structures of the isomers of N-Benzylideneaniline. J Am Chem Soc 93:4658

    Article  CAS  Google Scholar 

  22. de Silva SA, Loo KC, Amorelli B, Pathirana SL, Myakirang’ani DM, Demarais S, Dorcley B, Pullay P, Salih YA (2005) A fluorescent “off–on–off” proton switch derived from natural products and further studies of first-generation fluorescent photoinduced electron transfer (PET) systems. J Mater Chem 15:2791–2795

    Article  Google Scholar 

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Acknowledgments

We thank DST, New Delhi and UGC, New Delhi for financial assistance to the department through FIST and SAP respectively. UGC is also thanked for journal excess through INFLIBNET. IIT-Guwahati is thanked for HRM spectra.

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Authors and Affiliations

  1. Department of Chemistry, Gauhati University, Guwahati, Assam, India, 781 014

    Jutika Kumar, Manas Jyoti Sarma, Prodeep Phukan & Diganta Kumar Das

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  1. Jutika Kumar
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  2. Manas Jyoti Sarma
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  3. Prodeep Phukan
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  4. Diganta Kumar Das
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Correspondence to Diganta Kumar Das.

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Kumar, J., Sarma, M.J., Phukan, P. et al. Surfactant Dependent pH Controlled “off-on”, “off-on-off” and “on-off” Fluorescent Switches Exhibited by N-Benzylidenenaphthalen-1-Amine. J Fluoresc 25, 1431–1435 (2015). https://doi.org/10.1007/s10895-015-1633-y

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  • DOI: https://doi.org/10.1007/s10895-015-1633-y

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