Theoretical Investigation and Reconsideration of Intramolecular Proton-Transfer-Induced the Twisted Charge-Transfer for the Fluorescent Sensor to Detect the Aluminum Ion

doi:10.21203/rs.3.rs-1460369/v1

PDF

Research Article

Theoretical Investigation and Reconsideration of Intramolecular Proton-Transfer-Induced the Twisted Charge-Transfer for the Fluorescent Sensor to Detect the Aluminum Ion

https://doi.org/10.21203/rs.3.rs-1460369/v1

This work is licensed under a CC BY 4.0 License

Journal Publication

published 25 Apr, 2022

Read the published version in Structural Chemistry →

You are reading this latest preprint version

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) have 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 coordinate 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.

Aluminum sensor

Excited state intramolecular proton transfer

Fluorometric sensor

OFF-ON type

Twisted chargetransfer

Metal ions are closely related to the basic processes of living systems and human health problems [1–3]. Aluminum is the most abundant metal in the crust, and its elemental elements and compounds are widely used in production and life [4]. In recent years, the utilization of aluminum has been increased to food additives [5, 6], construction [7], medicine, ceramics, cosmetics and other fields. However, with the widespread use of aluminum and its alloys, the content of aluminum in soil and water gradually increased, resulting in the accumulation of Al³⁺ in food, water, air, etc. In addition, prolonged exposure to high levels of Al³⁺ is toxic to the kidney, liver, brain and nervous system [8–11]. Moreover, the abnormal concentration of Al³⁺ has adverse effects on the growth of seeds and root systems [12, 13]. Thus, timely monitoring of Al³⁺ levels in humans and the natural environment is needed to prevent the direct effects of Al³⁺ on the biosphere and human health [14]. In the previous report, the detection techniques have been defected because of the lack of coordination and spectrum performance. In recent years, chemical sensors used for monitoring biological and environment-related metal ions have been studied by researchers because of their advantages of simple synthesis route and high selectivity [15–19].

It is found that the closing sensor usually produces low signal output during binding, which can easily interfere with the time separation of similar compounds by time-resolved fluorescence method [20, 21]. Thus, many studies are inclined to the design and application of opening the sensor. Moreover, Al³⁺ is a fluorescence quencher due to its paramagnetism, which could affect the information of ‘turn-on’ fluorescent sensors for its detection [22–24]. In addition, selective binding of organic functional groups is one of the rational strategies for designing excellent fluorescent probes. Schiff base derivatives contain strong donor position (imine nitrogen atoms) which could provide a nitrogen-rich oxygen coordination environment [25, 26]. Moreover, Quinoline is also an ideal tool for metal ion fluorescence sensing based on good water solubility, good biocompatibility and large Stokes shift [27–29]. Generally, the practical chemical sensors mainly rely on various types of fluorescence mechanisms, such as ESIPT [30], photoinduced electron transfer (PET) and ICT mechanisms [31–33].

AHM is a sensor to show turn-on type, which is synthesized by Yadav et al [34]. The sensor AHM is consist of two parts, named A part and B part, which are connected by a carbon-nitrogen double bond (C = N), as shown in Scheme 1. Moreover, the imine nitrogen atom is able to transfer an electron to the hydroxyl-naphthalene, and the proton on the hydroxyl-naphthalene unit is transferred to the imine nitrogen, resulting in intramolecular hydrogen bond. Schiff bases bearing a C = N structure could easily isomerize and tend to exhibit very weak fluorescence. However, the Schiff base, with π electrons in C¼N group offers a good possibility for chelation with metal ions. Thus, when AHM and Al³⁺ form the complex, the C = N isomerization is inhibited and the fluorescence performance is enhanced. First, the presence of C = N double bonds may lead to a TICT. It is worth noting that there are two hydroxyl groups in AHM molecule, whether both can induce ESIPT reaction remains to be discussed, which are not considered in the experiment. Meanwhile, the photophysical characteristics of sensor AHM are complicated and the detection mechanism of sensor AHM and Al³⁺ is also lack of theoretical research. Here, the photophysical properties and sensing mechanism of AHM will be investigated. The charge transfer process is studied by hole-electron analysis and the variation of various parameters. In addition, the possible non-emission channels are studied by relaxation scanning. The detection mechanism of the sensor is analyzed in detail by studying the three-coordination structure between Al³⁺ and the sensor.

Computation details

1. All calculations were accomplished with the Gaussian16 program package [35] by using DFT and TDDFT methods. B3LYP functional [36] and TZVP basis set [37, 38] were selected to serve the calculation. The B3LYP functional is of 20% Hartree-Fock exchange, and has a low requirement for lattice point integration. In addition, the polarizable continuum model using the integral equation formalism variant (IEFPCM) was applied with acetonitrile (ACN) as the solvent simulating the experiment environment [39].

2. We optimize the structures of AHM-a, AHM-b and AHM-c in the S₀ and S₁ states without setting any restrictions on symmetry, bonds, angles, and calculate the IR frequencies in the same calculation level. It is proved that the molecular structures of our optimized AHM-c are at the local lowest point. The only imaginary frequency along with hydrogen bond orientation represents the transition-state structure of ESIPT reaction.

3. The calculated electron spectra are comparable with the experimental value, which show the reliability of the selected theoretical calculation method. Moreover, the charge transfer process is studied by hole-electron analysis. The degree of charge transfer is measured using the value of the centroid distance (D) index, the degree of overlap (S_r), the width distribution (H), degree of separation (t), hole delocalization index (HDI) and electron delocalization index (EDI), which are introduced by using the Multiwfn program [40, 41]. All the formulas are as follows:

\({D}_{x}\)=\(\left|{X}_{ele}-{X}_{ℎole}\right|\)\({D}_{y}\)=\(\left|{Y}_{ele}-{Y}_{ℎole}\right|\)\({D}_{Z}\)=\(\left|{Z}_{ele}-{Z}_{ℎole}\right|\)

D index=\(\sqrt{{\left({D}_{x}\right)}^{2}+{\left({D}_{y}\right)}^{2}+{\left({D}_{z}\right)}^{2}}\)

\({S}_{r}\)index =\(\int {S}_{r}\left(r\right)dr\)≡\(\int \sqrt{{\rho }^{ℎole}{\left(r\right)\rho }^{ele}\left(r\right)}\)dr

H index= (\(\left|{\sigma }_{ele}\right|\)+\(\left|{\sigma }_{ℎole}\right|\))/2

t index = D index-\(\left|H.{u}_{CT}\right|\)

HDI = 100×\(\sqrt{\int {\left[{\rho }^{ℎole}\left(r\right)\right]}^{2}dr}\)

EDI = 100×\(\sqrt{\int {\left[{\rho }^{ele}\left(r\right)\right]}^{2}dr}\)

4. We have used Multiwfn software to study the type of hydrogen bond interaction by applying RDG function. The formula is as follows:

RDG(r) =\(\frac{1}{{2\left({3\pi }^{2}\right)}^{1/3}}\frac{\left|\varDelta \rho \left(\text{r}\right)\right|}{{\rho \left(r\right)}^{4/3}}\)

The weak interactions depend on the λ₂ of eigenvalue and the ρ of electron density in view of Bader’s atoms-in-molecules (AIM) theory. The relationship between them is as follows:

Ω(r) = Sign (λ₂(r) )ρ(r)

Geometrical information of fluorescent sensor AHM

The sensor AHM has been optimized in the S₀ state. The optimized geometric structures are shown in Fig. 1b (referred to AHM-a). In Table 1, the ∠C₃C₂N₁C₄ is 157°, meanwhile, two single bonds, named C₂–N₁ and C₄–C₅ are observed, and the rotation between the single bonds makes the structure of AHM more flexible. Additionally, the distance between H₂-N₁ is 3.66Å, and there is no intramolecular hydrogen bond between them. However, there is a hydrogen bond between H₁ and N₁ with a bond length of 1.64 Å and the O₁H₁N₁ angle of 149°, which prevents the rotation of the intramolecular single bond. Thus, it is not necessary to consider the rotation forces caused by the C₄-C₅ deformation. To investigate the rotation of the C₂-N₁ single bond, relaxation scanning of the C₃C₂N₁C₄ dihedral is performed. We have obtained a rotamer with a C₃C₂N₁C₄ dihedral angle of 47°, abbreviated as AHM-b (Fig. 1a). Furthermore, Fig. 1d shows that in the S₀ state, the relative energy of AHM-a structure is 2.6 kcal/ mol lower than that of the AHM-b structure, which indicates that AHM-a is more stable. Thus, structure AHM-a is likely to exist.

Table 1

Geometrical information of chemical sensor AHM
	∠C₃C₂N₁C₄	∠C₂N₁C₄C₅	∠O₁H₁N₁	O₁-H₁	H₁-N₁
AHM-a-S₀	157°	177°	149°	1.01Å	1.64Å
AHM-b-S₀	47°	179°	148°	1.01Å	1.63Å
AHM-c-S₀	138°	177°	138°	1.70Å	1.03Å
AHM-d-S₀	137°	-12°	129°	0.97 Å	2.40 Å
AHM-TICT	-179°	91°	144°	0.98Å	1.84Å
AHM-c-S₁	173°	-179°	148°	1.58Å	1.05Å
^[a] All the data are obtained at the B3LYP/TZVP theory level.

Excitation and emission process of AHM

In order to explore the photophysical properties of the sensor, the excitation and emission process of AHM were further analyzed. The calculated wavelengths and other data are listed in Table 2. As seen in Table 2, the S₀→S₁ transition for AHM-a is predicted at about 403 nm with oscillator strength of 0.7211, and the process is from HOMO to LUMO. For S₀→S₁ of AHM-a, during the excitation process, the distribution region of the electron does not change significantly, which also means that the excitation of S₀→S₁ is a local excitation (LE). Here, hole-electron analysis is also used. And only 0.08 electrons are transferred between the A part and B part. In addition, as listed in Table 3, the D index is relatively small, which provides direct evidence for proving that S₀→S₁ is LE state. The proton transfer reaction, triggered by a strong hydrogen bond between H₁ and N₁, could generate the new isomer AHM-c (Fig. 1c) was obtained by the ground state relaxation scanning the distance between H₁ and N₁. As shown in Table 1, ∠C₃C₂N₁C₄ and ∠C₂N₁C₄C₅ are 138°and 177°, respectively. As depicted in Fig. 1d, the product AHM-c is more stable than AHM-a. Also, the GSIPT energy barrier from AHM-a to AHM-c is merely 2.4 kcal/mol which indicates that the AHM-c structure is the most likely configuration. Consequently, the excitation and emission process of AHM-c will be further explored.

As is reported in Table 2, the dominant transition of AHM-c is the S₀→S₁ transition, with the oscillator strength of 0.5271 lying at 410 nm, which is assigned to HOMO→LUMO (98.1%) transition. The orbitals are plotted in Fig. 2. A total of 0.16 electrons are transferred from the A part to the B part during the excitation, and the charge transfer is not obvious. Moreover, the D index is relatively small, which means that the S₀→S₁ of AHM-c is a LE state. The geometry in the S₁ state is optimized and given in Fig. 3a and Table 1. The C₃C₂N₁C₄ dihedral angle is 173°, which means there is a near planar structure in the S₁ state. The fluorescence quenching is not caused by planar structure. As listed in Table 2, AHM-c is a bright state in the S₁ state, and its oscillator strength is 0.9065. The calculated emission peak is 504 nm, which is consistent with the experimental value (500 nm). As is shown, the HOMO mainly distributes on the A part and B part while LUMO mainly distributes on the A part and C = N part. According to the hole-electron analysis, the charge transfer amount is relatively small (0.14 e). It is worth noting that the emission intensity observed at 500nm in the experiment is very weak, so the existence of a non-emission deactivation channel is assumed.

Table 2

Excitation and emission energies of the AHM, including the oscillator strength (f) and orbital transition (OT) contributions to the electronic exited states (CI).
	transition	λ(nm/eV)	f	OT	CI(%)
Experiment
absorption		400/3.10
emission		500/2.48
AHM-a-S₀	S₀→S₁	403/3.07	0.7211	H→L	98.3%
	S₀→S₂	327/3.78	0.0406	H-1→L	90.3%
	S₀→S₃	315/3.92	0.0508	H-2→L H→L + 2	85.6% 5.4%
	S₀→S₄	300/4.12	0.0315	H→L + 1	87.9%
AHM-b-S₀	S₀→S₁	403/3.07	0.5952	H→L	95.4%
	S₀→S₂	339//3.65	0.0123	H-1→L	90.1%
	S₀→S₃	317/3.91	0.0836	H-2→L H→L + 3	88.5% 7.3%
	S₀→S₄	299/4.14	0.0178	H→L + 1	92.3%
AHM-c-S₀	S₀→S₁	410/3.02	0.5271	H→L	98.1%
	S₀→S₂	349/3.55	0.0246	H-1→L	40.6%
	S₀→S₃	336/3.68	0.1087	H-1→L	51.3%
	S₀→S₄	308/4.02	0.0806	H-2→L	42.3%
AHM-c-S₁	S₁→S₀	504/2.45	0.9065	L→H	99.4%
AHM-TICT	S₁→S₀	4016/0.30	0.0001	L→H	99.4%
AHM-a-S₀, AHM-b-S₀ and AHM-c-S₀ represent S₀ state structures of a, b and c respectively. AHM-c-S₁ represents S₁ state structures of c. All the data are obtained at the B3LYP/TZVP theory level.

Table 3

The exponent of the excited states for the sensor AHM, including the centroid distance (D), the degree of overlap (S_r), the width distribution (H), degree of separation (t), hole delocalization index (HDI) and electron delocalization index (EDI).
	D(Å)	S_r	H(Å)	t(Å)	HDI	EDI
AHM-a S₀→S₁	0.63	0.73	3.45	-0.86	6.31	7.42
AHM-a S₀→S₃	1.66	0.74	3.18	-2.32	6.66	7.22
AHM-b S₀→S₁	0.68	0.69	3.33	-1.58	6.66	7.94
AHM-c S₀→S₁	0.72	0.71	3.26	-1.77	7.06	7.93

The origination of the non-emissive behavior of AHM

Generally, bending of the C = N double bond may result in the formation of non-luminous isomers. As shown in Fig. 4, the bending degree of AHM-a in the S₀ state was studied by relaxing and scanning the dihedral angle of C₂N₁C₄C₅. The ∠C₂N₁C₄ of AHM-a-S₀ (Fig. 4a) and AHM-d-S₀ (Fig. 4c) structure are 124°and 122°,respectively. As shown in Fig. 5, the structure of AHM-a in the S₁ state was firstly optimized, and a distorted structure was found. The local HOMO is delocalized through the B part, and LUMO is mainly localized on the C = N and A part, with complete charge separation. Furthermore, a total of 0.40 electrons are transferred from the left moiety to the right moiety during the S₁→S₀ excitation by using hole-electron analysis. As listed in Table 1, ∠C₃C₂N₁C₄ and ∠C₂N₁C₄C₅ are − 179°and 91°, respectively. Moreover, by TDDFT calculation, the oscillator strength is almost zero (0.0001). This indicates that in the S₁ state, AHM-a is a typical TICT state and then named as AHM-TICT. However, the bending angle of the N₁-C₄ double bond requires the energy of 30.17 kcal/mol. Thus, the TICT state cannot be attained by direct excitation and excited state relaxation from AHM-d-S₀.

In order to explore the pathway to the TICT state, the H₁-N₁ distance of AHM-c in the S₁ state was relaxed-scanned. As shown in Fig. 6, the energy barrier of ESIPT from AHM-c-S₁ to the transition state is merely 2.08kcal/mol. Moreover, the product produced by ESIPT happens to be AHM-a-S₁, also known as AHM-TICT, which indicates that ESIPT triggers the distortion of the structure and spontaneously reaches the TICT state. Due to the higher energy barrier from AHM-a to AHM-d, it is difficult to form AHM-d structure. In the S₁ state, AHM-c carries out ESIPT process and further triggers the TICT state.

IR vibrational spectra and RDG isosurfaces of sensor AHM

See in Fig. S1, the IR spectra of the main hydrogen bonds involved in the S₀ and S₁ states have been computed. For the AHM, the O₁-H₁ peak shifts from 3563 cm^− 1 in the S₀ state to 2945 cm^− 1 in the S₁ state. The IR vibrational frequency of O₁-H₁ bond of AHM has a red shift of 618 cm^− 1, which indicates that the AHM sensor has a large Stokes shift. It can also be manifested that the intramolecular hydrogen bond in S₁ state is much stronger than that in S₀ state through the analysis of stretching vibration frequencies.

As shown in the RDG scatter graph of Fig. S2 (a), the value range of the RDG isosurfaces is set from − 0.05 to 0.05. The spike peaks of the AHM complex are observed and located at -0.0408 (Fig. S2 (b)). The interaction type is assigned to hydrogen bond interaction and the more to the left of the peak, the stronger the hydrogen bond is. In the diagram, it can be seen that the part representing the hydrogen bonding interaction in O₁-H₁^…N₁ presents a ring in the RDG isosurfaces. There is a strong hydrogen bond interaction between H proton and N receptor in the S₁ state.

Al³⁺sensing mechanism of AHM

In the previous sections, the photo-physical process of the AHM was clarified. Next, the Al³⁺ detecting mechanism is explored. The reaction sites of hydrogen bonded donor and acceptor and their interactions can be analyzed by electrostatic potential (ESP). As shown in Fig. 7a, the ESP surface of AHM in the S₀ state is studied. The yellow ball and the blue ball correspond to the maximum and minimum values of the electrostatic potential respectively. The most negative site is located near O₁ atom, and its value is -125kJ/mol. Thus, the interaction between Al³⁺ and the O₁ position should be strong. Then, the complex formed between AHM and Al³⁺, is optimized, shown in Fig. 7b. Detailed geometric parameters are listed in Table 4. In order to ensure the rationality of the configuration in the coordination regions, Mayer bond order analyses of the AHM-Al is conducted through the Multiwfn program. The Mayer bond orders of three bonds (Al-O₁, Al-O₂, Al-N₁) are 0.73, 0.72, 0.53 respectively. These results indicate that the bonds of the Al-O₁, Al-O₂ and Al-N₁ are the coordinate bond. And the coordinate bond of Al-O₁ and Al-O₂ are stronger than Al-N₁ coordinate bond in the AHM-Al complexes.

As listed in Table 4, the structure of AHM-Al in the S₁ state is very similar to that in the S₀ state. In the S₁ state, the flatness of the molecule increases and the non-emitting TICT state is eliminated. Furthermore, the HOMO and LUMO orbitals of the ligand (AHM-a) and the complexes (AHM-Al) are also compared and analyzed. The energy gaps between HOMO and LUMO are found as 3.526 eV and 2.479 eV, respectively, for AHM-a and AHM-Al complex (Fig. 8). This indicates that AHM-Al complex is more stabilized than that of AHM-a. For AHM-Al, the electron is confined to the A part, and the distribution region of the electron does not change significantly before and after the excitation. Meanwhile, the emission process of AHM-Al is studied. As shown in Table 5, the S₁→S₀ emission with large oscillator strength of 0.9313 generates π→π* transition character, which means the AHM-Al is emissive. Moreover, Al³⁺is not involved in the emission process, who eliminates the original TICT state.

Table 4

eometries of the complex (at B3LYP/TZVP theory level).
	AHM-Al-S₀	AHM-Al-S₁
∠C₃C₂N₁C₄	149°	153°
∠C₂N₁C₄C₅	-161°	-169°
∠N₁C₄C₅C₆	19°	16°
Al-O₁	1.79Å(0.73)	1.72Å(0.74)
Al-O₂	1.84Å(0.72)	1.77Å(0.71)
Al-N₁	1.95Å(0.53)	1.85Å(0.55)
^[a] The values in the brackets are calculated Mayer bond orders. ^[42]

Table 5

Excitation and emission energies of the metal-sensor complexes (B3LYP/ TZVP).
	transition	λ(nm/eV)	f	OT	CI (%)
AHM-Al-S₀	S₀→S₁	431/2.87	1.2638	H→L	94.4%
	S₀→S₂	422/2.94	0.0214	H→L H-1→L	50% 38%
	S₀→S₃	411/3.01	0.1623	H-1→L	92%
AHM-Al-S₁	S₁→S₀	530/2.34	0.9313	L→H	97%
^aAHM-Al represents the triple-coordinated organometallic compound formed between AHM and Al³⁺.

In conclusion, the sensor AHM has been researched and analyzed by DFT and TDDFT theoretical methods. The imine nitrogen of the sensor is adjacent to the -OH group, and the sensor has a large spectral shift for Al³⁺ ions due to the presence of polar groups such as hydroxyl and amine. Furthermore, the trivalent form of these groups has a high affinity for the Al³⁺ ion. In acetonitrile solvent, the AHM exhibits weak fluorescence emission because of ESIPT and C = N isomerization. Upon adding of Al³⁺, the AHM coordinates with the metal ions and eliminates the TICT state. The coordination Al³⁺ with AHM deprotonates the phenolic hydroxyl groups preventing the intrahydrogen bonding with imine nitrogen (O-H^…N) and also inhibits the ESIPT. Based on the characteristics of sensor AHM, it is widely used in real life, such as cell imaging and dipstrip test.

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)and the General Program from Education department of Liaoning Province (Grant LJKZ0534).

Conflicts of interest The authors declare no competing interest.

Availability of data and material Not applicable

Code availability Not applicable

Authors' contributions The data collection, analysis, writing were performed by Xiumin Liu. The data collection, analysis were performed by Hengwei Zhang. The data analysis was performed by Sen Liu.The study’s conception, design, data collection, analysis, writing, editing, review, and supervision were performed by Yi Wang.The study’s conception, editing, review, and supervision were performed by Peng Zhang.

HeZL, Yang, XE, Stoffella PJ (2005) Trace elements in agroecosystems and impactson 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 Jr JA et al (2015) Recognition-andreactivity-based fluorescent probes for studying transition metal signaling inliving systems. Acc Chem Res48:2434–2442.https://doi.org/10.1021/acs.accounts.5b00221
Sorenson JR, Campbell IR, Tepper LB et al (1974) Aluminum in theenvironment and human health. Environ Health Perspect8:3–95.https://doi.org/10.1289/ehp.7483
Litov RE, Sickles VS, Chan GM et al (1989) Plasmaaluminum measurements in term infants fed human milk or a soy-based infant formula.Pediatrics84:1105–1107.
Yokel RA, Hicks CL, Florence RL (2008) Aluminum bioavailability from basicsodium aluminum phosphate, an approved food additive emulsifying agent,incorporated in cheese. Food Chem Toxicol46:2261–2266.https://doi.org/10.1016/j.fct.2008.03.004
Soni MG, White SM, Flamm WG et al (2001) Safety evaluation of dietaryaluminum. 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 theUnited States: part 2–trichloroethylene and 1, 1, 1-trichloroethane. EnvironForensics 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. Metallomics4:56–65. https://doi.org/10.1039/c1mt00139f
Mirza A, King A, TroakesC et al (2017) Aluminium in brain tissue in familial Alzheimer's disease. Journal of trace elements in medicine and biology: organ of the Society for Minerals and Trace Elements. 40:30–36.https://doi.org/10.1016/j.jtemb.2016.12.001
Nayak P (2002) Aluminum: impacts and disease. Environ Res89:101–115.https://doi.org/10.1006/enrs.2002.4352
Good PF, Olanow C, Perl DP (1992) Neuromelanin-containing neurons of thesubstantia nigra accumulate iron and aluminum in Parkinson’s disease: aLAMMA study. Brain Res593:343–346.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 Chem9:5523−5529. https://doi.org/10.1039/c1ob05479a
Zhao Q, Li F, Huang C (2010) Phosphorescent chemosensors based on heavy-metalComplexes. Chem SocRev39:3007–3030.https://doi.org/10.1039/b915340c
Zhang JF, Zhou Y, Yoon J et al (2011) Recent progress in fluorescent andcolorimetric chemosensors for detection of precious metal ions (silver, goldand platinum ions). Chem Soc Rev40:3416–3429.https://doi.org/10.1039/c1cs15028f
Kaur K, Saini R, Kumar A et al (2012) Chemodosimeters: an approach for detection and estimation of biologicallyand medically relevant metal ions, anions and thiols. Coord Chem Rev256:1992–2028.
Yang Y, Zhao Q, Feng W et al (2013) Luminescent chemodosimeters for bioimaging. ChemRev113:192–270.https://doi.org/10.1021/cr2004103
Schneider HJ, Yatsimirsky AK (2000) Principles and Methods in SupramolecularChemistry. J Wileyhttps://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. Soc129:10322-10323. 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. OrgLett9:33–36. 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 Lett51:618–621. 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, H. J.; 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
Fang TC, Tsai HY, Luo MH et al (2013) Excited-state chargecoupled 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
Jana S, Dalapati S, Guchhait N (2012) Proton transfer assisted charge transferphenomena in photochromic schiff bases and effect of–NEt2 groups to the AnilSchiff bases.J Phys Chem A116:10948–10958.https://doi.org/10.1021/jp3079698
Li W, Tian X, Huang B et al (2016) Triphenylamine-based Schiff bases as theHigh sensitive Al³⁺or Zn²⁺fluorescence turn-on probe: mechanism and application in vitro and in vivo,Biosens Bioelectron77:530–536.https://doi.org/10.1016/j.bios.2015.09.059
Rodríguez-Córdoba W, Zugazagoitia JS, Collado-Fregoso E et al (2007) Excitedstate intramolecular proton transfer in schiff bases. Decay of the locallyexcited enol state observed by femtosecond resolved fluorescence. J PhysChem A111:6241–6247.https://doi.org/10.1021/jp072415d
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 Fluoresc27:723–728. https://doi.org/10.1007/s10895-016-2003-0
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
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
Neetu Yadav, Ashok Kumar Singh (2018)A turn-on ESIPT based fluorescent sensor for detection of aluminum ion withbacterial cell imaging and logic gate applications.Materials Science & Engineering C 90:468-475. https://doi.org/10.1016/j.msec.2018.04.087
Frisch MJ, Trucks GW, Schlegel HB et al (2016) Gaussian, Inc., Wallingford CT.
Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A38:3098–3100.
Schafer A, Horn H, Ahlrichs R (1992) Fully optimized contracted Gaussian basis sets for atoms Li to Kr. J Chem Phys97:2571–2577.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 Phys100:5829–5835.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 Phys107:3032–3041.https://doi.org/10.1063/1.474659
Lu T, Chen FW (2012) Multiwfn: A multifunctional wavefunction analyzer. J Comput Chem 33:580–592. 10.1002/jcc.22885
Johnson ER. Keinan S, Sanchez PM et al (2010) Revealing noncovalent interactions. J Am Chem Soc132:6498–6506.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.

PDF

Journal Publication

published 25 Apr, 2022

Read the published version in Structural Chemistry →

Reviews received at journal
24 Mar, 2022
Reviewers invited by journal
24 Mar, 2022
Editor assigned by journal
21 Mar, 2022
First submitted to journal
16 Mar, 2022

You are reading this latest preprint version

Theoretical Investigation and Reconsideration of Intramolecular Proton-Transfer-Induced the Twisted Charge-Transfer for the Fluorescent Sensor to Detect the Aluminum Ion

Status:

Journal Publication

Version 1

Abstract

Figures

Introduction

HDI = 100×\(\sqrt{\int {\left[{\rho }^{ℎole}\left(r\right)\right]}^{2}dr}\)

EDI = 100×\(\sqrt{\int {\left[{\rho }^{ele}\left(r\right)\right]}^{2}dr}\)

Results And Discussion

Conclusions

Declarations

References

Status:

Journal Publication

Version 1