Abstract
A Schiff base compound 6-amino-5-(((2-hydroxynaphthalen-1-yl)methylene)amino)-2-mercaptopyrimidin-4-ol (AHM) in acetonitrile solvent is found to show “OFF–ON type” mode upon addition of Al3+ ion and successfully applied for selective recognition of Al3+ ion. In this work, the reconsideration of excited state intramolecular proton transfer (ESIPT) and twisted intramolecular charge transfer (TICT) has been explored in detail based on density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods. In the absence of Al3+, the lone pair electrons are transferred from –C = N to –OH forming a hydrogen-bonding configuration, and AHM shows weak fluorescence. When AHM is coordinated with metal ion, the TICT state is eliminated, and emission is significantly enhanced. Thus, in this paper, the origination of the non-emissive behavior of AHM has been explained in detail. The frontier molecular orbitals (MOs) and hole-electrons are used to analyze the charge distribution, providing strong evidence for the possibility of ESIPT and TICT processes occurring.
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He ZL, Yang XE, Stoffella PJ (2005) Trace elements in agroecosystems and impacts on the environment. J Trace Elem Med Biol 19:125–140. https://doi.org/10.1016/j.jtemb.2005.02.010
Aron AT, Ramos-Torres KM, Cotruvo JA Jr et al (2015) Recognition-and reactivity-based fluorescent probes for studying transition metal signaling in living systems. Acc Chem Res 48:2434–2442. https://doi.org/10.1021/acs.accounts.5b00221
Sorenson JR, Campbell IR, Tepper LB et al (1974) Aluminum in the environment and human health. Environ Health Perspect 8:3–95. https://doi.org/10.1289/ehp.7483
Litov RE, Sickles VS, Chan GM et al (1989) Plasma aluminum measurements in term infants fed human milk or a soy-based infant formula. Pediatrics 84:1105–1107
Yokel RA, Hicks CL, Florence RL (2008) Aluminum bioavailability from basic sodium aluminum phosphate, an approved food additive emulsifying agent, incorporated in cheese. Food Chem Toxicol 46:2261–2266. https://doi.org/10.1016/j.fct.2008.03.004
Soni MG, White SM, Flamm WG et al (2001) Safety evaluation of dietary aluminum. Regul Toxicol Pharm 33:66–79. https://doi.org/10.1006/rtph.2000.1441
Doherty RE (2000) A history of the production and use of carbon tetrachloride, tetrachloroethylene, trichloroethylene and 1, 1, 1-trichloroethane in the United States: part 2–trichloroethylene and 1, 1, 1-trichloroethane. Environ Forensics 1:83–93. https://doi.org/10.1006/enfo.2000.0011
House E, Esiri M, Forster G et al (2012) Aluminium, iron and copper in human brain tissues donated to the medical research council’s cognitive function and ageing study. Metallomics 4:56–65. https://doi.org/10.1039/c1mt00139f
Mirza A, King A, Troakes C et al (2017) Aluminium in brain tissue in familial Alzheimer’s disease. J Trace Elem Med Biol 40:30–36. https://doi.org/10.1016/j.jtemb.2016.12.001
Nayak P (2002) Aluminum: impacts and disease. Environ Res 89:101–115. https://doi.org/10.1006/enrs.2002.4352
Good PF, Olanow C, Perl DP (1992) Neuromelanin-containing neurons of the substantia nigra accumulate iron and aluminum in Parkinson’s disease: a LAMMA study. Brain Res 593:343–346. https://doi.org/10.1016/0006-8993(92)91334-b
Yumoto S, Kakimi S, Ishikawa A (2009) Demonstration of aluminum in amyloid fibers in the cores of senile plaques in the brains of patients with Alzheimer’s disease. J Inorg Biochem 103:1579–1584. https://doi.org/10.1016/j.jinorgbio.2009.07.023
Rondeau V, Jacqmin-Gadda H, Commenges D et al (2009) Amuminum and silica in darking water and the risk of Alzheimer’s disease or cognitive decline: findings from 15-year follow-up of the PAQUID cohort. Am J Epidemiol 169:489–496. https://doi.org/10.1093/aje/kwn348
Sahana A, Banerjee A, Das S et al (2011) A naphthalene-based Al3+ selective fluorescent sensor forliving cell imaging. Org Biomol Chem 9:5523–5529. https://doi.org/10.1039/c1ob05479a
Zhao Q, Li F, Huang C (2010) Phosphorescent chemosensors based on heavy-metal complexes. Chem Soc Rev 39:3007–3030. https://doi.org/10.1039/b915340c
Zhang JF, Zhou Y, Yoon J et al (2011) Recent progress in fluorescent and colorimetric chemosensors for detection of precious metal ions (silver, gold and platinum ions). Chem Soc Rev 40:3416–3429. https://doi.org/10.1039/c1cs15028f
Kaur K, Saini R, Kumar A et al (2012) Chemodosimeters: an approach for detection and estimation of biologically and medically relevant metal ions, anions and thiols. Coord Chem Rev 256:1992–2028. https://doi.org/10.1016/j.ccr.2012.04.013
Yang Y, Zhao Q, Feng W et al (2013) Luminescent chemodosimeters for bioimaging. Chem Rev 113:192–270. https://doi.org/10.1021/cr2004103
Schneider HJ, Yatsimirsky AK (2000) Principles and methods in supramolecular chemistry. J Wiley. https://doi.org/10.1002/9783527644131
Zhang M, Yu MX, Li FY et al (2007) A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging. J Am Chem Soc 129:10322–10323. https://doi.org/10.1021/ja073140i
Zhao M, Ma L, Zhang M et al (2013) Glutamine-containing “turn-on” fluorescence sensor for the highly sensitive and selective detection of chromium (III) ion in water. J Spectrochim Acta Part A 116:460–465. https://doi.org/10.1016/j.saa.2013.07.069
Wu JS, Liu MW, Zhuang XQ (2007) Fluorescence turn on of coumarin derivatives by metal cations: a new signaling mechanism based on C=N isomerization. Org Lett 9:33–36. https://doi.org/10.1021/ol062518z
Tang XL, Peng XH, Dou W et al (2008) Design of a semirigid molecule as a selective fluorescent chemosensor for recognition of Cd(II). Org Lett 10:3653–3656. https://doi.org/10.1021/ol801382f
Li L, Dang YQ, Li HW et al (2010) Integrated genomic analyses of ovarian carcinoma. Tetrahedron Lett 51:618–621. https://doi.org/10.1038/nature10166
Liu YJ, Tian FF, Fan XY et al (2017) Fabrication of an acylhydrazone based fluorescence probe for Al3+. Sensors Actuators B Chem 240:916–925. https://doi.org/10.1016/j.snb.2016.09.051
Upadhyay Y, Bothra S, Kumar R, Choi HJ (2017) Sahoo, S K. Optical sensing of hydrogen sulphate using rhodamine 6G hydrazide from aqueous medium. Spectrochim Acta A 180:44–50. https://doi.org/10.1016/j.saa.2017.02.057
Stasiuk GJ, Minuzzi F, Sae-Heng M et al (2015) Dual-modal magnetic resonance/fluorescent zinc sensors for pancreatic β-cell mass imaging. Chem Eur J 21:5023–5033. https://doi.org/10.1002/chem.201406008
Mummidivarapu VVS, Tabbasum K, China JP et al (2012) 1,3-di-amidoquinoline conjugate of calix[4]arene(L)as a ratiometric and colorimetric sensor for Zn2+:spectroscopy, microscopy and computational studies. Dalton Trans 41:1671–1674. https://doi.org/10.1039/c2dt11900e
Yu FS, Guo XF, Tian XJ et al (2017) A ratiomeric fluorescent sensor for Zn2+ based on N, N’-Di(quinolin-8-yl)oxalamide. J Fluoresc 27:723–728. https://doi.org/10.1007/s10895-016-2003-0
Rodríguez-Córdoba W, Zugazagoitia JS, Collado-Fregoso E et al (2007) Excited state intramolecular proton transfer in schiff bases. Decay of the locally excited enol state observed by femtosecond resolved fluorescence. J Phys Chem A 111:6241–6247. https://doi.org/10.1021/jp072415d
Li W, Tian X, Huang B et al (2016) Triphenylamine-based Schiff bases as the high sensitive Al3+ or Zn2+ fluorescence turn-on probe: mechanism and application in vitro and in vivo. Biosens Bioelectron 77:530–536. https://doi.org/10.1016/j.bios.2015.09.059
Jana S, Dalapati S, Guchhait N (2012) Proton transfer assisted charge transfer phenomena in photochromic schiff bases and effect of–NEt2 groups to the Anil Schiff bases. J Phys Chem A 116:10948–10958. https://doi.org/10.1021/jp3079698
Fang TC, Tsai HY, Luo MH et al (2013) Excited-state charge coupled proton transfer reaction via the dipolar functionality of Salicylideneaniline. Chin Chem Lett 24:145–148. https://doi.org/10.1016/j.cclet.2013.01.011
Yadav N, Singh AK (2018) A turn-on ESIPT based fluorescent sensor for detection of aluminum ion with bacterial cell imaging and logic gate applications. Mater Sci Eng C 90:468–475. https://doi.org/10.1016/j.msec.2018.04.087
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ (2016) Gaussian 16 Revision C.01. Gaussian Inc. Wallingford CT
Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 38:3098–3100. https://doi.org/10.1103/physreva.38.3098
Schafer A, Horn H, Ahlrichs R (1992) Fully optimized contracted Gaussian basis sets for atoms Li to Kr. J Chem Phys 97:2571–2577. https://doi.org/10.1063/1.463096
Schafer A, Huber C, Ahlrichs R (1997) Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr. J Chem Phys 100:5829–5835. https://doi.org/10.1063/1.467146
Cances E, Mennucci B, Tomasi J (1997) A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics. J Chem Phys 107:3032–3041. https://doi.org/10.1063/1.474659
Liu ZY, Lu T, Chen QX (2020) An sp-hybridized all-carboatomic ring, cyclo[18]carbon: electronic structure, electronic spectrum, and optical nonlinearity. Carbon 165:461–467. https://doi.org/10.1016/j.carbon.2020.05.023
Le Bahers T, Adamo C, Ciofini I (2011) A qualitative index of spatial extent in charge-transfer excitations. J Chem Theory Comput 7:2498–2506. https://doi.org/10.1021/ct200308m
Lu T, Chen FW (2012) Multiwfn: a multifunctional wavefunction analyzer. J Comput Chem 33:580–592. https://doi.org/10.1002/jcc.22885
Johnson ER, Keinan S, Sanchez PM et al (2010) Revealing noncovalent interactions. J Am Chem Soc 132:6498–6506. https://doi.org/10.1021/ja100936w
Mayer I (1983) Charge, bond order and valence in the AB initio SCF theory. Chem Phys Lett 97:270–274. https://doi.org/10.1016/0009-2614(83)80005-0
Funding
This work was supported by the Open Project of SKLMRD (the open fund of the state key laboratory of molecular reaction dynamics in DICP, CAS), the General Program from Education department of Liaoning Province (Grant LJKZ0534) and Basis Research Project of Department of Education of Liaoning Province (Grant J2019020).
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Xiumin Liu performed data collection, analysis, and writing. Hengwei Zhang performed data collection and analysis. Sen Liu performed data analysis. Yi Wang performed the study’s conception, design, data collection, analysis, writing, editing, review, and supervision. Peng Zhang performed the study’s conception, editing, review, and supervision.
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Liu, X., Zhang, H., Liu, S. et al. Theoretical investigation and reconsideration of intramolecular proton-transfer-induced the twisted charge-transfer for the fluorescent sensor to detect the aluminum ion. Struct Chem 33, 1355–1364 (2022). https://doi.org/10.1007/s11224-022-01941-z
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DOI: https://doi.org/10.1007/s11224-022-01941-z