Design, Photochemistry, Logic Gates Behavior and Antibacterial Evaluation of novel ICT systems based on 1,8- naphthalimides

doi:10.21203/rs.3.rs-2007530/v1

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Design, Photochemistry, Logic Gates Behavior and Antibacterial Evaluation of novel ICT systems based on 1,8- naphthalimides

https://doi.org/10.21203/rs.3.rs-2007530/v1

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Ace Naphthene as a primary material was nitrated and further reacted by various unit processes such as oxidation, imidation and amination in order to obtain dyad 5. The Dyad 5 fluorescence in solvents of different polarity is shifted bathochromically with increasing the solvent polarity due to ICT enhancement, fluorescent enhancement is greatest in case of chloroform (Ф_F = 0.48) Excitation at 420 nm ,The influences of the pH on dyad 5 were also investigated, the results can be considered as representing off-on-off states. dyad 5 executes two input XNOR logic gates, the dyad 5 shows optical sensing towards H⁺ and HO⁻ ions, it was investigated the “off-on-off” switching behavior of the receptor between H⁺ and HO⁻ ions, the synthesized compounds were tested for antimicrobial activity of Gram-positive and Gram-negative bacteria, compounds were tested have a good antibacterial activity as compared with standard compound (Gentamycin).

Fluorescence

(XNOR)Logic Gates

ICT

“off-on-off” switching

Antibacterial evaluation

A significant goal in the field of nanotechnology is the design of multi-functional molecular devices with built-in individually functional components which are working cooperatively as a whole ^[1]. Supramolecular devices that show large changes in their so called “off” and “on” states are currently of great interest as these can be modulated, or tuned, by employing external sources such as ions, molecules, light, etc. ^[2–5].

The “off” and “on” states of the molecular-level devices refer to their luminescence, magnetic or electronic properties. The binary possibilities where the signal change was large enough to be considered as “off-on” or “on-off” are increasingly conscious of information technology. Following the concept of molecular logic proposed by Aviram ^[6], de Silva demonstrated experimentally the analogy between molecular switches and electronic logic gates ^[7]. Since then, a large number of significant logic functions were exploited ^[8–10]. In particular, fluorescent systems and their excited-state processes (charge- or electron transfer, energy transfer, proton transfer) have been frequently employed in the rational design of molecular logic devices ^[11]. These molecules capable of carrying out a variety of sensing functions simultaneously, and that compute a composite result autonomously, have great potential for real-life applications such as object coding and imaging, intelligent materials, drug delivery and activation, diagnostics or actuation ^[12–15]. In nearly two decades, all 16 fundamental logic gates ^[16–19] and more complex systems such as half-adder/subtractor ^[20], full-adder/subtractor ^[21], multiplexer ^[22], encoder/decoder ^[23], digital comparator ^{[24, 25]} and keypad lock ^[26] were demonstrated.

Also a smart oligonucleotide-based constructs playing simple games such as Tic–Tac–Toe ^[27] and molecular scale “anticancer destroyer” ^[28] have been reported. Nevertheless, the physical integration of molecular logic gates is especially important for rational design and implementation toward advanced molecular scale computing. Two common principles for fluorescence molecular switches are used: photoinduced electron transfer (PET) and internal charge transfer (ICT) ^{[29, 30]} .

Fluorescent PET systems based on the “fluorophore–spacer–receptor” format are the most commonly exploited approach for the design of the fluorescent sensors and switches ^[31]. The components are chosen so that PET from electron rich receptor (usually an amino group) to the fluorophore excited state quenches the fluorescence of the system. Upon recognition of guest, which binds to the receptor, engaging its lone-pair electrons, the PET process is no longer possible and the fluorescence of the system is recovered ^[32]. In contrast with PET systems, in the ICT chemosensors the receptor is directly attached to the electrondonating/withdrawing unitthatis conjugated to the fluorophore an electron-withdrawing/electron-donating unit ^{[33, 34]}. During excitation of the system the fluorophore undergoes donor–acceptor intramolecular charge transfer which strongly depends on the microenvironment of the fluorophore. Thus recognition of guest affects the ICT efficiency that changes the energy between ground and excited state and results in shifting of the fluorophore electronic spectra ^{[35, 36]}. The amalgamation of PET and ICT pathways has provided examples of multilevel logic systems with multiple logic functions, including arithmetic operations by modulation of the fluorescence output ^[37–40]

In all cases the shape and the maximum of the fluorescence band do not depend of the excitation wavelength and the excitation spectra are identical to the corresponding absorption. spectra. Scheme 1 schematic representation of electron transfer to an ICT excited state of fluorophore for 5, scheme 1 .

Melting points were measured using an Electrothermal IA 9100 apparatus with open capillary tube and are uncorrected. The IR spectra (KBr disc) were recorded on PyeUnicam Sp-3-300 or a Shimadzu FT-IR 8101 PC infrared spectrophotometer. The 1H NMR spectra were measured on a JEOL-JNM-LA 400 MHz (100 MHz) spectrometer using DMSO-d6 as a solvent. All chemical shifts were expressed on the d (ppm) scale using TMS as an internal standard reference. The coupling con[1]stant (J) values are given in Hz.

Synthesis of 4-nitro acenaphthene (2)

To a solution of 20 g acenaphthene (0.13 mol) in 40ml dichloroethane, 24 ml of nitric acid (48%) was added dropwise at 10-15^oC for a period of 30 min. The reaction mixture was stirred for 1 h at this temperature. Then the precipitate was collected by filtration, washed with water and dried. The pure product was obtained after recrystallization from acetic acid (85 %). M.p. 100-101^оС. Yield 22.8 g (88%).

Synthesis of 4-nitro-1,8-naphthalic anhydride ( 3) :

To a solution of 15 g 4-nitro acenaphthene (0.13 mol) in 150 ml acetic acid, 58 g of potassium bichromate was added portion wise at 80^oC for a period of 2 h. The resulting mixture was stirred for 5 h at 90^oC then poured into 100 ml of water. The crude precipitate was collected by filtration, washed with water and dissolved in 200ml 5% aqueous sodium hydroxide. The unsoluble fraction was removed after filtration and the product that precipitated after acidification of the filtrate to pH 4 was collected and dried at 120^oC, to give pure 4-nitro-1,8-naphthalic anhydride.

IR (KBr) cm-1: 1780 -1760 (nN-C=O); 1520 -1310 (nNO2)., 1Н NMR (DMSO-d6, 250.13 MHz) ppm: 9.40(d, 1H, J=8.6 Hz, naphthalimide H-7); 9.59 (d, 1H, J=7.2 Hz,naphthalimide H-5); 9.33 (d, 1H, J=8.6 Hz, naphthalimide H-2); 8.35(t, 1H, J=7.9 Hz, naphthalimide H-6); 8.72 (d,1H, J=8.8 Hz, naphthalimide H-3)

Synthesis of 4-nitro-N-allyl-1,8-naphthalimide (4) :

4-nitro-1,8-naphthalic anhydride (3) (2.8 g, 0.01 mol) was dispersed in ethanol (50 mL) and allylamine (0.012 mol, 20% excess) was added at 55°C. The solution was refluxed for 3-4 h; the liquor was then cooled and the product was filtered, washed with water and dried in vacuo at 30°C . 4- nitro-N-allyl-1,8-naphthalimide was characterized using FTIR and 1H NMR , FTIR (KBr) ν = 1592 cm^-1 C-NO₂ str.; 1581 cm^-1 C=C str.; 1662, 1702 cm^-1 C=O str. Carbonyl; 3072 cm^-1 =C-H str. 1H NMR (DMSO-d6 , 400 MHz) δ = 2.38-2.41 (2H, NCH₂CH=CH₂ ); 5.03-5.08 (2H, NCH₂CH=CH₂ ); 5.89-5.93 (1H, NCH₂CH=CH₂ ); 7.9 (1H, 6-H); 8.13 (1H, 5-H); 8.2 (1H, 7-H); 8.42 (1H, 2- H); 8.48 (1H, 3-H). ). Elemental analysis :Calculated for C₁₅H₁₀N₂O₄ (MW 282.25) C 63.60, H 3.30, N 9.72%; Found C 63.83, H 3.57, N 9.92%.

Synthesis of 1,8-naphthalimide (5) :

4-Nitro-1,8-naphthalimide 4 (0.85 g, 3.0 mmol) was added to 5 mL of hydrazine monohydrate. The reaction mixture was refluxed for 2 h under stirring then poured into water. The precipitate was collected by filtration, washed with water and dried to yield N-allyl[1]1,8-naphthalimide 5 as a yellow solid (0.78 g, 97%). FT-IR (KBr) cm⁻¹: 3433 (nNH), 3314 (nNH₂); 1673 (nasN C O); 1633 (nsN C O). 1H NMR (CDC_l3-d, 250.13 MHz) ppm: 8.61 (d, 1H, J = 8.0 Hz, Naphthalimide H-2); 8.58 (d, 1H, J = 7.9 Hz, Naphthalimide H-7); 8.26(d, 1H, J = 8.1 Hz, Naphthalimide H-5); 7.66 (dd, 1H, J = 7.9 Hz, J = 8.1 Hz, Naphthalimide H-6); 7.39 (d, 1H, J = 8.0 Hz, Naphthalimide H-3); 5.94 (m, 1H, NCH₂CH CH₂); 5.10 (d, 1H, Jtrans = 16.5 Hz, allyl HCH ); 5.25 (d, 1H, Jcis = 9.3 Hz, allyl HCH ); 4.79 (br.s, 1H, NH); 4.61 (d, 2H, J = 5.7 Hz, CH2CH CH2); 2.38 (br.s, 2H, NH2). Elemental analysis :Calculated for C₁₅H₁₃N₃O₂ (MW 267.28) C 67.40, H 4.90, N 15.72%; Found C 67.65, H 5.08, N 15.39%.

Antibacterial Screening of the Synthesized compounds:

The biological activity of the resulting compounds was studied on Gram (+) (Bacillus subtilis) and Gram (-) (Escherishia coli and p.Aerogus.) bacteria by preparing liquid media (from yeast extract, beef extract, peptone and sodium chloride in water). Every type of the bacteria used was dissolved in an amount of this media in two different sterilized vessels and it was left for 24 hours to give suitable size of bacterial growth. One gram sample of every synthesized material in the pervious experiments was prepared by putting in Pasteur tube as column, then the liquid bacterial solution was added and left to flow by the action of the earth gravity and the turbidity of the solution was measured after and before passing from the column using spectrophotometer (with wave length 560 cm^-1). A comparison was made to determine the effect of the material on the bacteria after passing from the column.

The solid material was packed into glass Pasteur pipettes 5.75 inches long, 0.25 inches inside diameters the sample was washed with pH 7.0 chlorine-demand-free water until no free chlorine could be detected in the elute water. The particle size for some of the polymer samples was sufficiently small that compressed nitrogen was used to force the inoculum through the column to enhance flow rates.

Another experiment was done by using nutrient agar media (solid media prepared using yeast extract, agar, beef extract, sodium chloride and peptone in distilled water) in different dishes, two dishes for every material one for Gram (+) and the other for Gram (-) and a pore was made in the middle of the media in every dish then the 0.005 grams/l (in DMF) of solid material was added to this pore. The dishes were put at 37°C for 24 hours and the inhibition zone was measured in every dish and the results was tabulated to know the direct effect of the materials, and a photos were taken for every dish ^[41,42].

Design and synthesis of 1,8-naphthalimide (5)

The 4-hydrazino-1,8-naphthalimide 5 represents the “fluorophore-receptor” architecture with ICT chemosensing properties, where the 4-amino-1,8-naphthalimide is fluorophore and amino group possessing labile protons is a receptor moiety. The fragments with labile N-H bonds widely are used in anion recognition because the acidity of the NH group can be easily tuned by adjusting the electronic properties of neighboring substituents so that it can recognize anions through hydrogen-bonding or deprotonation interactions.

It is well known that absorption and fluorescence characteristics of the 1,8-naphthalimides depend on the nature of the substituent at C-4 position of the 1,8-naphthalimide ring .The 4-amino-1,8-naphthalimide is a “push-pull” π-electron system in which the light absorption generates a charge transfer interaction between C-4 amine donating substituent and the both peri-positioned carbonyl acceptors (Scheme 2) .

The novel compound were prepared in basic steps: synthesis of 4-nitro-1,8-naphthalic anhydride, synthesis of amino functional yellow-green emitting 1,8-naphthalimide donors, The starting 4-nitro-1,8-naphthalic anhydride 3 was prepared in two steps as shown in (schemes 1-2) . First, 4-nitro-acenaphtene 2 was obtained by nitration of acenaphtene 1 with 48% nitric acid. Then the intermediate compound 2 was converted into the desire 4-nitro-1,8-naphthalic anhydride 3 after oxidation with sodium bichromate. The imidation of aromatic cyclic anhydride is a nucleophilic displacement reaction in which allylamine is the attacking group, and this reaction is carried out in alcoholic media under reflux conditions .In this reaction, nitro group remains on naphthalene ring and it is not replaced with allylamine. In this reaction,4-nitro- N- allyl-1,8-naphthalimide 4 was prepared with high purity, then reaction of the 1,8-naphthalimide 4 with hydrazine monohydrate in ethanol to give the fluorescent target compound 5 with high purity (scheme 3,4)

The abosorbtion of 5 in solvents of different polarity is shifted bathochromically with increasing the solvent polarity due to ICT enhacement with increasing solvent polarity which leads to solvation, a large dipole moment which results bathochromic shift of absorption in 5 (Figure 1) .

Table 1 . Photophysical characteristics of 5 in different solvents (Excitation at 420 nm).

Solvent	λ_A (nm)	λ_F (nm)	ν_A – ν_F (cm^-1)	Ф_F
DMF	438	522	3673	0.16
Ethanol	440	528	3787	0.22
Chloroform	422	505	3894	0.48
Acetonitrile	440	522	3570	0.24

In all cases the shape and the maximum of the ﬂuorescence band do not depend of the excitation wavelength and the excitation spectra are identical to the corresponding absorption spectra.

Influence of pH on the absorption and fluorescence characteristics of 1,8-naphthalimide (5):

The compound 5 under study was designed as fluorescence sensors for determining pH changes over a wider pH scale. This was the reason to investigate the photophysical behaviour of compound 5 in water/DMF (3:1, v/v) solution at different pH values and investigation in water/DMF due to aggregation of the compound 5 in pure water.

The influence of pH on the absorbance of 5 is illustrated in the Figs. 2-3. Upon addition of sodium hydroxide from pH 2.38 to pH 4 the wavelength absorption is bathochromic shifted. The major reason is that in very acidic conditions the push–pull character of the ICT state is decreased due to the protonation of the 4-amino moiety itself (compound 5) that decreased the “push-pull” character of the ICT transition and caused a considerable decrease of the absorption band. Addition of sodium hydroxide from pH 4 to pH 10 bathochromically shifted the absorption wavelengths as well. However, the major reason is that in very alkaline conditions the push–pull character of the ICT state is increased due to the deprotonation of the 4-amino moiety itself (compound 5) that increased the “push-pull” character of the ICT transition and caused a considerable increase of the absorption band.

Addition of sodium hydroxide from (PH=10 to PH=13.27) leads to appearance of novel band at 550 nm due to that ICT reduced this one attributed to deprotonation of 4-amino-1,8-naphthalimide in the presence of NaOH.

The fluorescence spectra of compound 5 were also recorded in water/DMF (3:1, v/v) solution at different pH values (Figs. 4-5).

Upon addition of NaOH solution the fluorescence intensity of 1,8-naphthalimide 5 as a function of pH in water/DMF (3:1, v/v) was gradually increased in range of pH = 2.38 to 8.50 as demonstrated in Fig. 4. With addition of excess amount of NaOH the emission intensity at 542 nm had enhanced. Under very acidic conditions the push-pull character of the ICT state is decreased due to the protonation of the 4-amino moiety of compound 5 that caused a considerable decrease of the fluorescence intensity. Furthermore, the addition of NaOH from pH 8.50 to 13.27 to compound 5 causes gradually decreases of the emission as demonstrated in Fig. 5. This is due to the deprotonation of the amine moiety in the presence of NaOH excess.

These changes are of such magnitude that they can be considered as representing two different “states”, where the fluorescence emission is “switched off” in acidic solution, “switched on” in neutral solution and “switched off” in alkaline solution (Fig. 6). The changes in the fluorescence intensity as a function of pH for compound 5 should be related to the protonation of its amine receptor in acidic solution and deprotonation of the amine receptor in strong alkaline solution.

Molecular logic gates for 1,8-naphthalimide (5) :

With single input (analyte binding H⁺) and single output (e.g., “switch-on” of fluorescence intensity) only two simple operations are possible, YES when input is 0 or 1 and the output is the same, and NOT, which is the opposite - when input is 0 or 1, the output is 1 or 0. Fluorescent “off-on” sensors where an analyte causes a fluorescence enhancement (FE) can be understood as YES logic gates . A logical inverter, some-times called a NOT gate reverses the logic state and it would be implement on molecular level using “on-off” sensors which fluorescence is quenched in the presence of an analyte (OH^-).

More complicated logical operations are possible with two inputs such as two different ions bound to two different sites. There are six basic logic gates that oper-ate with two inputs and one output: AND, OR, XOR, NAND, NOR and XNOR. And all of this logic gates were achieved by molecules The AND gate is so named because, if 0 is called “false” and 1 is called “true,” the gate acts in the same way as the logical “and” operator. The output is “true” when both inputs are “true.” Otherwise, the output is “false”.

The XNOR (exclusive-NOR) gate is a combination of XOR gate followed by an inverter. Its output is “true” if the inputs are the same and “false” if the inputs are different. Since the receptor 5 shows optical sensing towards H⁺ and HO^- ions, it was investigated the “off-on-off” switching behavior of the receptor between H⁺ and HO^- ions. The addition of H⁺ ions to the solution of compound 5 at pH=8 leads to fluorescence quenching, that is, “off-state”. And at pH=8 fluorescence emission is “on-state”. The addition of HO^- ions to the solution of 5 at pH = 8 (“off-state”). Such fluorescence changes upon the actions of two chemical inputs mimic the performance of an exclusive-NOR (XNOR) logic gate (Table 1).

Table 1 : Truth table for XNOR logic gate of 5 with two chemical inputs (H⁺ and HO^-).

Compound 5 At PH 8	Input H⁺	Input HO^-	Output Fl
	0	0	1
	1	0	0
	0	1	0
	1	1	1

Antibacterial evaluation of the synthesized dyes:

Some of the synthesized compounds were tested for antimicrobial activity using the agar diffusion method ^[41,42] against representatives of Gram-positive bacteria (Bacillus subtilis) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) (Table 2). Compounds 3, 4 and 5 have excellent results against Gram-negative bacteria (E. coli) and the most effective compound against Gram-negative bacteria (E. coli and P. aeruginosa) is 5 and inhibition zone for compound 6 is 18 and 17 mm, respectively, and the best result against Gram-positive bacteria for compound 3 while inhibition zone is 15 mm, in general compounds were tested have a good antibacterial activity as compared with standard compounds (Gentamycin).

Table 2: Mean zone of inhibition in mm produced on a range of pathogenic microorganisms results are depicted in the following table.

Selected samples	3	4	5	Control
Tested microorganisms	Mean IZ	Mean IZ	Mean IZ	Mean IZ	± SD
Gram-positive bacteria				Gentamycin
Bacillus subtilis: RCMB 015 (1) NRRL B-543	15	17	15	26.02	0.03
Gram-negatvie bacteria				Gentamycin
Escherichia coli: (RCMB 010052) ATCC 25955	15	13	18	29.90	0.01
Pseudomonas aeruginosa	10	12	17	21.01	0.04

The test was done using the diffusion agar technique, well diameter: 6.0 mm (100 µl was tested), RCMB: Regional,Center for Mycology and Biotechnology.
Positive control for bacteria Gentamycin 4 µg/ml.
The sample was tested at 5 mg/ml concentration.

From the data present in Table 2 it is clear that, all compounds have effect upon gram positive and gram negative bacteria, compound no. 5 affects gram positive (Bacillus subtilis) 15 mm lower than gram negative (E. coli) 18 mm Furthermore, compounds no. 4 affects gram positive (Bacillus subtilis) 17 mm greater than gram negative (E. coli) 13 mm .while, compound no. 3 affects gram positive (Bacillus subtilis) and Escherichia coli gram negative similarly, in general 3,4 and 5 compounds which were tested have a good antibacterial activity as compared with standard compounds (Gentamycin) .

Acknowledgments authors acknowledge gratefully the financial support provided from Erasmus mundus association .

Authors ‘contributions: Alaa R. Sakr : investigation (writing , synthesis , photochemistry and spectral analysis ); Nikolai I. Georgiev: methodology, investigation ; Vladimir B. Bojinov : supervision ,writing , review and editing.

Funding research funding provided by Erasmus mundus scholarship (medastar program )

Data availability statement: authors are declare that the data supporting the findings of this study are available within the article

Code availability: chemdraw , origin

Declarations

Ethical approval not applicable

Consent to participate not applicable

Consent for publication not applicable

Conflict of interest there are no conflicts to declare

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Scheme 1 to 4 are available in Supplementary Files section.

No competing interests reported.

Scheme1.png
Scheme 1 Schematic representation of an ICT system based on 1,8- naphthalimide unit of dyad 5.
Scheme2.png
Scheme 2. Fluorescence changes of Dyad 5 in the presence of protons (0.01 M HCl), hydroxide anions (0.01 M NaOH) .
Scheme3.png
Scheme4.png
Supplementarymaterialfluorsencejournal.doc

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