Alternaria alternata from Calotropis procera leaves and Aspergillus terreus from Trigonella foenum-graecum seeds were able to counteract the lipopolysaccharide (LPS) pro-inflammatory effect on THP-1 cells differentiated into macrophages. Moreover, they were able to induce an anti-inflammatory state, rendering them less sensitive to the LPS pro-inflammatory stimulus. Taken together, these results show that these both endophytic fungi could be interesting alternatives to conventional anti-inflammatory drugs. To gain more detailed knowledge of their chemical richness, phytochemical analysis of the ethyl acetate extracts of the five endophytic fungi studied was performed using HPTLC, GC-MS and LC-MS with the Global Natural Products Social (GNPS) platform and the MolNetEnhancer tool. A large family of metabolites  were detected. The purification of endophytic fungus extract of Alternaria alternate, which diminished TNF-α production of 66% at 20 µg/mL, incubated one hour before LPS addition, led to the characterization of eight pure compounds. These molecules are altertoxins I, II, III, tricycloalternarenes 3a, 1b, 2b, anthranilic acid, and o-acetamidobenzoic acid. In the future, all these pure compounds will be evaluated for their anti-inflammatory activity, while altertoxin II has been shown in the literature as the most active mycotoxin in terms of anti-inflammatory activity.Patients suffering from inflammatory chronic diseases are classically treated with anti-inflammatory drugs but unfortunately are highly susceptible to becoming resistant to their treatment. Finding new drugs is therefore crucial and urgent and research on endophytic fungi is a promising way forward. Endophytic fungi are microorganisms that colonize healthy plants and live within their intercellular tissues. They are able to produce a large variety of secondary metabolites while allowing their host to stay healthy. A number of these molecules are endowed with antioxidant or antimicrobial as well as cytotoxic properties, making them very interesting/promising in the field of human therapy. The aim of our study was to investigate whether extracts from five endophytic fungi isolated from plants are endowed with anti-inflammatory activity. Extracts of the endophytic fungi  The incidence rate of chronic inflammatory disease is increasing and now constitutes a world health problem due to some factors such as the ageing population, lack of exercise, obesity, unhealthy food, sleep disturbance and environmental factors such as pollution ,2,3,4. PPatients suffering from inflammatory bowel disease or rheumatoid diseases such as arthritis, lupus or vasculitis are classically treated with steroidal anti-inflammatory drugs to diminish inflammation and pain ,6. In adThe search for new classes of anti-inflammatory molecules is therefore crucial, and finding new molecules which could be complementary or maybe even an alternative to the classical anti-inflammatory molecules will be useful not only for humans but also for other animals’ health.Penicillium notatum in 1922 + was identified as Altertoxin I, a perylenequinone compound, which matches with the molecular formula of C20H16O6.In cluster 5A, the ion peak at m/z 284.140 [M + H]+ was identified as 3-(1H-indol-3-ylmethyl)-2,3,6,7,8,8a-hexahydropyrrolopyrazine-1,4-dione or Cyclo(L-Pro-L-Trp), which matches the molecular formula of C16H17N3O2.Among them, in cluster 7A, the ion peak at Aspergillus terreus).Molecular network (MN) analysis of extracts B, C and D  have beeNetwork analysis revealed the presence of 12 classes/subclasses of chemical compounds annotated such as: lactones/delta valerolactones  corresponding to statin compounds; pyrimidodiazepines ; anthracenes/hydroxyanthraquinones ; fatty acyls/fatty acid esters ; steroids and steroid derivatives/bile acids, alcohols and derivatives (clusters 3B and 3C); prenol lipids/diterpenoids (clusters 5B and 6D); carboxylic acids and derivatives/amino acids, peptides and analogs (clusters 11B and 7C); lupin alkaloids/sparteine, lupanine and related alkaloids (cluster 3D); pyridines and derivatives/hydropyridines (cluster 5D); lactones/gamma butyrolactones (cluster 6B); benzene and substituted derivatives/diphenylethers (7B); phthalide isoquinolines (cluster 7D).The molecular network (MN) revealed that the three extracts  had the following classes/subclasses in common: lactones/delta valerolactones lactones, pyrimidodiazepines, phenols/1-hydroxy-2-unsubstituted benzenoids and fatty acyls/fatty acid esters.m/z 405.256, [M + H]+ was present, which matched the molecular formula of C24H36O5. The peak ion m/z 445.253 as [M + Na]+ corresponded to lovastatin hydroxy acid sodium salt with molecular formula C24H35O6.Lovastatin was annotated in the lactones/delta valerolactone and lactone clusters; according to the peak ion Aspergillus terreus extracts, and the lovastatin structure was confirmed via comparison with the commercially available standard and GC-MS analysis.These compounds were present in the three m/z 437.289, m/z 407.272 and m/z 447.268 as [M + H]+, corresponding to lovastatin-related compounds according MS/MS spectra.In extract B, we observed the peak ions m/z 297.071 as [M + H]+ which matched the molecular formula of C17H12O5  for [M + H]+ 297.075).In the clusters 8B, 8D and 10D, phenols/1-hydroxy-2-unsubstituted benzenoids were identified. In these networks, we observed the ion corresponding to Aspulvinone E, a yellow pigment found in Aspergillus, with peaks ions m/z 301.063 and 285.072 as [M + H]+ which matched the molecular formula of C16H12O6  and C16H12O5  respectively. Emodin  was identified only in cluster 10D, with 271.054 as [M + H]+.Several classes/subclasses were only common in two extracts. This was the case for anthracene/hydroxyanthraquinone networks , uniquely present in extracts B and D. Questinol and questin were annotated in the clusters 8B–8D and 12B–12D, with peak ions at Molecular network (MN) analysis of extract E revealed the presence of different classes/subclasses of chemical compounds . Clusterm/z 271.053 as [M + H]+  and the peak ion of m/z 255.06 as [M + H]+ were identified as genistein and daidzein , respectively.In cluster 4E, the peak ion of Alternaria alternata constitutes the most interesting of the five fungal endophytic extracts based on its strong anti-inflammatory and cytotoxic activity (1), altertoxin II (compound 2) and altertoxin III (compound 3); three tricycloalternarenes, tricycloalternarene 3a (compound 4), tricycloalternarene 2b (compound 5) and tricycloalternarene 1b (compound 6); and two nitrogen compounds, anthranilic acid (compound 7) and o-acetamidobenzoic acid (compound 8) were identified. The chemical structures are presented in the As extract A from activity , its eth1, i.e., altertoxin I ; 317.0759 [M-2H2O + H]+  299.0615 [M-3H2O + H]+ ; 289.0781 [M-2H2O-CO + H]+  and 271.0699 [M-3H2O-CO + H]+ . MSMS spectra data matched Pubchem data.For the characterization of compound rtoxin I , the expC20H17O6 . MSMS sp13C NMR spectrum revealed two carbonyl groups resonating at 207.0 and 204.8 ppm  visible on the COSY spectrum  by observing the C-9/H-8α correlation tasks; C-9/H-8β; C-4/H-5α; C-4/H-5β and C-9b/H-6b.In addition, the confirmation of the chaining of the hydrocarbon skeleton of altertoxin I was carried out via exploration of the HMBC spectrum , making 2, i.e., altertoxin II ; 315.0607 [M-2H2O + H]+ ; 305.0789 [M-H2O-CO + H]+ ; 287.0646 [M-2H2O-CO + H]+ ; 263.0658 [M-H2O-CO-O-ChCH + H]+ or [C17H10O3 + H]+ . Compound 2 was determined to be an analog of compound 1, based on the comparison of their 1D NMR data and 2D NMR analyses ; 303.0600 [M-HCOOH + H]+ ; 275.0650 [M-HCOOH-CO + H]+ ; 247.0705 [M-HCOOH-2CO + H]+ ; 219.0760 [M-HCOOH-3CO + H]+  and 191.0824 [M-HCOOH-4CO + H]+ . The isolated compound 3 was very unstable, as it darkened on the columns during purification and on the TLC plates and even in the NMR tube 30 min after sample preparation. The analysis of its 1H NMR spectrum ; 295.2045 [M-2H2O + H]+ ; 277.1907 [M-3H2O + H]+ , and then the loss of CHx matched the carbonated structure. The structure was confirmed via 1D NMR data and the 2D NMR analyses  each, appearing at δH = 1.65 ppm and δH = 1.55 ppm; an integrating doublet for three protons (3H), appearing at δH = 0.93 ppm with a coupling constant J = 6.8 Hz; an integrating multiplet for a proton (1H), appearing at δH = 5.02 ppm; an integrating multiplet for two protons (2H), appearing at δH = 1.84 ppm; two integrating multiplets for one proton (1H) each, appearing at δH = 1.45 ppm and δH = 1.28 ppm; and an integrating multiplet for a proton (1H), appearing at δH = 1.96 ppm. On the 1H-1H COSY spectrum (1H NMR spectrum (J = 5.6 Hz. These protons were carried by the carbons δC = 119.8 ppm (sp2) and δC = 66.6 ppm (oxygenated carbon), respectively ; 311.2048 [M-2H2O + H]+ ; 293.1839 [M-3H2O + H]+  and then the loss of CHx matches with carbonated structure. MSMS spectra matched spectra suggested by Pubchem. Compound 5 was determined to be an analog of compound 4, based on the comparison of their 1D NMR data and the 2D NMR analyses , relative to the proton of one of the two methyl groups of the isoprenoid derivative and the appearance of a singlet around 3.95 ppm integrating for two protons (2H). These observations directed us towards a tricycloalternarene with a structure similar to that of tricycloalternarene 3a and possessing an oxygenated methylene group in position 2 of the side chain. The absence of methoxy protons in the proton deshielding region (3.4–3.9 ppm) led us to believe that the oxygen radical was a simple hydroxyl. The analysis of the HSQC spectrum  and then the loss of CHx matched carbonated spectra. Compound 6 was determined via a study of 1D NMR data and the 2D NMR analyses  or potassium (K), such as 448.0840 for [3(C7H7NO2) + K-2H]− (cacld. 448.0916). MSMS spectra showed a fragment at 92.0509 [M-CO2-H]− (cacld. 92.0506). MSMS spectra matched spectra suggested by Pubchem.For the characterization of compound lic acid , the analic acid , indicat7 was determined via study of 1D NMR data and the 2D NMR analyses ; 134.0610 [M-CO2-H]− (cacld. 134.0611) and 92.0539 [M-CH2CO-CO2-H]− (cacld. 92.0506). The study of 1D NMR and the 2D NMR analyses were carried out to confirm this structure  and 54% (60 µg/mL), respectively, one hour after LPS. Only these two extracts were able to inhibit the pro-inflammatory effect of LPS. Moreover, they were able to induce an anti-inflammatory state rendering of THP-1 cells less sensible to the LPS pro-inflammatory stimulus. We have shown previously that extract C had also antioxidant activity (IC50 18.01 ± 0.1 µg/mL) + m/z 353.1025, found: 353.0973.Compound 2, altertoxin II, was obtained as a yellow crystal. 1H NMR : δ (ppm) 8.07 , 7.98 , 7.04 , 6.98 , 4.33 , 3.67 , 3.55 , 3.19 , 2.86 , 2.77 , 2.47 . 13C NMR : δ (ppm) 206.4 (C-4), 199.0 (C-9), 164.0 (C-3), 163.5 (C-10), 141.2 (C-9b), 136.9 (C-1), 134.1 (C-12), 136.9 (C-12c), 126.2 (C-12a), 124.8 (C-12b), 119.8 (C-2), 117.7 (C-11), 115.4 (C-9a), 115.0 (C-3a), 69.1 (C-6a), 57.2 (C-7), 54.3 (C-8), 46.3 (C-6b), 34.2 (C-5), 33.8 (C-6). HRESIMS (positive mode) calcd. for C20H15O6 [M + H]+ m/z 351.0869, found: 351.0844.Compound 3, altertoxin III, was obtained as a powder. 1H NMR : δ (ppm) 11.49 (4-OH), 11.49 (10-OH), 7.60 , 7.60 , 6.90 , 6.90 , 4.60 , 4.60 , 4.22 , 4.22 , 3.86 , 3.86 . HRESIMS (positive mode) calcd. for C20H13O6 [M + H]+ m/z 349.0712, found: 349.0677.Compound 4, tricycloalternarene 3a, was obtained as a colorless oil. 1H NMR : δ (ppm) 5.02 , 5.31 , 2.77 , 2.58 , 2.55 , 2.55 , 2.46 , 4.33 , 2.21 , 2.18 , 1.96 , 1.92 , 1.84 , 1.65 , 1.55 , 1.48 , 1.45 , 1.28 , 0.93 . 13C NMR : δ (ppm) 196.8 (C-18), 169.9 (C-14), 150.4 (C-7), 131.5 (C-2), 124.6 (C-3), 119.8 (C-8), 108.0 (C-13), 88.9 (C-10), 66.6 (C-15), 46.8 (C-11), 45.0 (C-9), 35.0 (C-5), 33.7 (C-17), 32.4 (C-6), 29.0 (C-16), 26.0 (C-4), 25.8 (C-1), 23.8 (C-10′), 20.3 (C-6′), 17.8 (C-2′), 15.5 (C-12). HRESIMS (positive mode) calcd. for C21H31O3 [M + H]+ m/z 331.2273, found: 331.2303.Compound 5, tricycloalternarene 2b, was obtained as a white solid. 1H NMR : δ (ppm) 5.32 , 5.24 , 4.02 , 3.95 , 2.77 , 2.70 , 2.57 , 2.48 , 2.45 , 2.34 , 2.30 , 2.14 , 2.01 , 1.70 , 1.90–1.98 , 1.61 , 1.47 , 1.43 , 1.33 , 0.96 . 13C NMR : δ (ppm) 197.9 (C-18), 173.0 (C-14), 150.2 (C-7), 135.4 (C-2), 125.6 (C-3), 120.1 (C-8), 105.2 (C-13), 88.9 (C-10), 71.1 (C-17), 68.9 (C-1), 46.7 (C-11), 45.2 (C-9), 34.8 (C-5), 31.3 (C-6), 29.6 (C-16), 27.9 (C-15), 25.0 (C-4), 23.4 (C-10′), 20.3 (C-6′), 15.1 (C-12), 13.8 (C-2′). HRESIMS (positive mode) calcd. for C21H31O4 [M + H]+ m/z 347.2222, found: 347.2226.Compound 6, tricycloalternarene 1b, was obtained as a white solid. 1H NMR : δ (ppm) 5.31 , 4.03 , 3.42 , 2.74 , 2.64 , 2.57 , 2.48 , 2.44 , 2.39 , 2.30 , 2.19 , 2.00 , 1.73 , 1.56 , 1.43 , 1.43 , 1.24 , 1.31 , 1.24–1,3 , 1.02 , 0.95 , 0.87 . 13C NMR : δ (ppm) 198.0 (C-18), 172.6 (C-14), 150.6 (C-7), 119.9 (C-8), 105.4 (C-13), 88.5 (C-10), 71.1 (C-17), 68.5 (C-1), 46.6 (C-11), 45.1 (C-9), 35.6 (C-2), 35.2 (C-5), 33.2 (C-3), 32.6 (C-6), 29.7 (C-16), 27.9 (C-15), 24.8 (C-4), 23.5 (C-10′), 20.3 (C-6′), 16.7 (C-2′), 15.5 (C-12). HRESIMS (positive mode) calcd. for C21H33O4 [M + H]+ m/z 349.2378, found: 349,2472.Compound 7, anthranilic acid, was obtained as a colorless crystal. 1H NMR : δ (ppm) 7.70 , 7.12 , 6.63 , 6.47 . 13C NMR : δ (ppm) 171.7 (C-1), 152.8 (C-3), 134.9 (C-2), 133.4 (C-6), 116.6 (C-4), 116.6 (C-7) 115.0 (C-5). HRESIMS (negative mode) calcd. for C7H6NO2 [M − H]− m/z 136.0398, found: 136.0353.Compound 8, o-acetamidobenzoic acid, was obtained as a colorless crystal. 1H NMR : δ (ppm) 8.45 , 8.00 , 7.57 , 7.16 , . 13C NMR : δ (ppm) 169.9 (C-1), 169.1 (C-8), 141.1 (C-3), 133.9 (C-5), 131.5 (C-7), 123.0 (C-6), 120.3 (C-4), 118.1 (C-2), 25.4 (C-9). HRESIMS (negative mode) calcd. for C9H8NO3 [M − H]− 178.0510, found: 178.0553.Compound We report, for the first time, anti-inflammatory activity screening and an extensive metabolomics analysis of extracts providing from five endophytic fungi isolated from Sudanese medicinal plants. The anti-inflammatory activity screening has opened the way to discover active endophytic fungi crude extracts, and the metabolomics analysis has permitted us to detail their chemical richness. The HPTLC, GC-MS and LC-MS analyses combined with molecular networking data processing were carried out to allow the identification of different structures of metabolites such as fatty acids, carboxylic acids and derivatives, steroid derivatives, alkaloids, hydroxyanthraquinones, valerolactones and perylenequinones. Based on literature data, a number of molecules belonging to perylenequinone family could have anti-inflammatory activities.Aspergillus terreus and extract A from Alternaria alternata) were able to inhibit the LPS pro-inflammatory effect on differentiated THP-1 cells. Moreover, these both extracts were able to set these cells in an anti-inflammatory state rendering them less sensible to the pro-inflammatory LPS effect.We found that two extracts (extract C from Alternaria alternata exhibited the strongest anti-inflammatory activity. Its purification showed the presence of three perylenequinones such as altertoxins, three terpenoids such as tricycloalternarenes and two derivatives of benzoic acid. These perylenequinones and in particular, altertoxin II could explain this anti-inflammatory activity.Extract A from However, due to limited literature data, the terpenoid compounds with the tricycloalternares structures, need also to be investigated for this biological property.


The compound based on 2,2-diphenyl-6-aza-1,3-dioxa-2-stannanaphthopyridocyclononene revealed the formation of a monomeric complex with a distorted five-coordinated molecular geometry intermediate between the trigonal bipyramidal and square pyramidal. In order to find possible applications in photovoltaic devices, hybrid films of organotin(IV) complexes embedded in poly:poly(styrenesulfonate) (PEDOT:PSS) with graphene were deposited. The topographic and mechanical properties were examined. The film with the complex integrated into the cyclohexyl substituent has high plastic deformation, with a maximum stress of 1.69 × 107 Pa and a Knoop hardness of 0.061. The lowest values of 1.85 eV for the onset gap and 3.53 eV for the energy gap were obtained for the heterostructure having the complex with the phenyl substituent. Bulk heterojunction devices were fabricated; these devices showed ohmic behavior at low voltages and a space-charge-limited current (SCLC) conduction mechanism at higher voltages. A value of 0.02 A was found for the maximum carried current. The SCLC mechanism suggests hole mobility values of between 2.62 × 10−2 and 3.63 cm2/V.s and concentrations of thermally excited holes between 2.96 × 1018 and 4.38 × 1018 m−3.The synthesis of four pentacoordinated organotin(IV) complexes prepared in a one-pot reaction from 2-hydroxy-1-naphthaldehyde, 2-amino-3-hydroxypyridine and organotin oxides is reported. The complexes were characterized by UV-Vis, IR, MS,  Thin-film organic photovoltaic technology has been the subject of considerable attention because of the advantages it provides, such as light devices and low preparation cost ,2,3,4. WKeeping the above in mind, and in order to broaden the study of different tin coordination structures, in this work, we report the synthesis of four pentacoordinated organotin(IV) complexes prepared in a one-pot reaction from 2-hydroxy-1-naphthaldehyde, 2-amino-3-hydroxypyridine and organotin(IV) oxides. This work is divided into three parts: the first one corresponds to the synthesis and characterization of the pentacoordinated organotin(IV) complexes; the second one refers to the fabrication and characterization of poly:poly(styrenesulfonate) (PEDOT:PSS)-graphene-organotin(IV) complex hybrid films, and the third one refers to the manufacture and electrical characterization of devices made from the hybrid films. It is important to mention that PEDOT:PSS is one of the best-known conjugate polymers that have proved their value in the development of electronic devices. PEDOT:PSS provides excellent optoelectronic functionalities, as highly transparent and electrochemically stable conducting films can be obtained from its doped state. The combination of PEDOT:PSS with chemically different structures, such as graphene, permits the improvement of their electrical properties and their use in various kinds of photovoltaic applications ,34,35,36The behavior of organotin(IV) complexes is related to their π-conjugated structure, including the presence of electron-donating or electron-accepting substituents. This turns organotin(IV) complexes into anisotropic semiconductors with preferential conduction channels for charge transport. The novelty of this work is related to the synthesis of new pentacoordinated tin complexes and their use in hybrid films with optical and electrical properties.1a–1d were synthesized in a one-pot reaction. 2-Hydroxy-1-naphthaldehyde, 2-amino-3-hydroxypyridine and the corresponding organotin oxide in a stoichiometric ratio 1:1:1 were refluxed using a solvent mixture of toluene–methanol (80:20 v/v), as shown in 1a and 1c and their in vitro antibacterial activity have been previously described; however, the complexes were obtained in a two-step reaction, and the ligand was refluxed in methanol with dibutyl or diphenyl tin(IV) dichloride in the presence of Et3N as a base. On the other hand, neither the yields nor the complete NMR, mass spectrometry or UV-Vis characterization was reported , which is smaller than the ideal 180°. The major distortion in coordination geometry about the tin atom in compound 1c can be associated with the formation of five-membered  and six-membered  chelate rings, resulting in tight N1-Sn1-O1 [82.78(8)°] and N1-Sn1-O2 [78.45(9)°] chelate angles, which are shorter than 90°. Thus, the ONO Schiff base behaves as a tridentate coordinating ligand. Five- and six-membered rings result when the N-Sn coordination bond is formed. The annular tension of the formed cycles and the large covalent radius of the tin(IV) atom restrict the planarity of these complexes. The dihedral angles involving these chelate rings are in the range of 0.18(8)° to 6.70(9)°, indicating the non-planarity of the ligand plane around the tin atom  were obtained only for complex riptor τ , for whie values , the disatom see .1c, the Sn(1)-O(2) and Sn(1)-O(1) distances at the five- and six-membered rings are both 2.09(2) Å, close to the sum of the covalent radii of Sn-O atoms (2.10 Å), but smaller than that of Van der Waals radii for Sn and O atoms (3.75 Å). These values indicate that these complexes possess strong Sn-O bonds. The Sn(1)-N(1) bond distance is 2.15(2) Å and is equal to the sum of the covalent radii for Sn and N, suggesting a strong tin–nitrogen interaction. This value is comparable to those of analogous diorganotin(IV) complexes containing both five- and six-membered chelate rings, including a set of ONO donor atoms tin oxides were prepared using the method previously described in the literature .1H, 13C and 119Sn were acquired using the Bruker Avance III instrument  at 300 MHz, 400 MHz and HD 500 MHz in CDCl3. Direct analysis in real time (DART) mass spectra were recorded on a JEOL-JMS-T100LC instrument . The X-ray diffraction study was performed with a BRUKER SMART APEX CCD diffractometer  at a wavelength λ(Mo-Kα) = 0.71073 Ǻ (graphite monochromator) and temperature T = 298 K for complex 1c. The structure was solved using direct methods in the SHELXS program. All non-hydrogen atoms were anisotropically refined using a full-matrix, least-squares technique, and all hydrogen atoms were placed in idealized positions using the riding hydrogen model approximation. Structural solutions and refinements were performed using SHELXTL : 219 , 253  π → π* (aromatic), 363 (4034) π → π* (C=N), 483  n → π* (C=N); IR (ATR) cm−1: 3043 ν(C-H), 2948 νas(C-H), 2920 νas(C-H), 2865 νsim(C-H), 2846 νsim(C-H), 1601 ν(C=O), 606 ν(Sn-C), 548 ν(Sn-O), 483 ν(Sn-N); 1H NMR  δ: 0.85 , 1.34 , 1.50–1.55 , 1.61–1.72 , 6.89 , 7.07–7.08 , 7.33 , 7.56 , 7.67 , 7.78 , 7.81 , 8.26 , 10.48  = 52 Hz, H-11); 13C NMR  δ: 174.2 (C-1), 157.7 (C-11), 153.8 (C-16), 145.2 (C-12), 139.7 (C-3), 135.2 (C-13), 134.9 (C-9), 129.4 (C-5), 128.7 (C-7), 127.1 (C-4), 124.8 (C-2), 124.5 (C-14), 124.3 (C-15), 123.6 (C-6), 119.5 (C-8), 108.8 (C-10), 26.9 (2J(13C-117/119Sn) = 40 Hz, C-β), 26.6 (C-γ), 22.4 (C-α), 13.6 (C-δ); 119Sn NMR  δ: −191; MS: (DART+) [m/z] (%):  (33). HR-MS (DART+) m/z: 497.12151 , observed: 497.12384.Compound 1b was prepared from 0.236 g (1.365 mmol) of 2-hydroxy-1-naphthaldehyde, 0.151 g (1.365 mmol) of 2-amino-3-hydroxypyridine and 0.410 g (1.365 mmol) of dicyclohexyltin(IV) oxide, producing 0.409 g (55%) of a brown solid; m.p. 69–71 °C; molar conductance, ΛM : 7.9 μS cm−1; UV-Vis : 214 , 256  π → π* (aromatic), 347 (7285) π → π* (C=N), 485  n → π* (C=N); IR (ATR) cm−1: 2916 νas(C-H), 2845 νsim(C-H), 1599 ν(C=O), 601 ν(Sn-C), 548 ν(Sn-O), 488 ν(Sn-N); 1H NMR  δ: 1.50–2.17 , 6.93 , 7.06 , 7.11 , 7.32 , 7.55 , 7.67 , 7.76 , 7.81 , 8.27 , 10.56  = 49 Hz, H-11); 13C NMR  δ: 174.7 (C-1), 157.6 (C-11), 154.4 (C-16), 145.5 (C-12), 139.6 (C-3), 135.0 (C-9), 134.9 (C-13), 129.3 (C-5), 128.6 (C-7), 127.1 (C-4), 125.0 (C-2), 124.4 (C-14), 124.2 (C-15), 123.5 (C-6), 119.5 (C-8), 108.8 (C-10), 40.2 (1J(13C-119/117Sn) = 600, 574 Hz, C-α), 30.9 (2J(13C-119Sn) = 25 Hz, C-β), 28.6 (3J(13C-119/117Sn) = 94, 81 Hz C-γ), 26.6 (C-δ); 119Sn NMR  δ: −258; MS: (DART+) [m/z] (%):  (17); HR-MS (DART+) m/z: 549.15640 , observed: 549.15405.Compound 1c was prepared from 0.157 g (0.910 mmol) of 2-hydroxy-1-naphthaldehyde, 0.101 g (0.910 mmol) of 2-amino-3-hydroxypyridine and 0.2631 g (0.910 mmol) of diphenyltin(IV) oxide, producing 0.275 g (57%) of an orange solid; m.p. 148–150 °C; molar conductance, ΛM : 10.6 μS cm−1; UV-Vis : 220 , 255  π → π* (aromatic), 371 (7529) π → π* (C=N), 481  n → π* (C=N); IR (ATR) cm−1: 3044 ν(C-H), 2948 νas(C-H), 2921 νas(C-H), 2866 νsim(C-H), 2847 νsim(C-H), 1601 ν(C=O), 607 ν(Sn-C), 550 ν(Sn-O), 485 ν(Sn-N); 1H NMR  δ: 7.11 , 7.19 , 7.28 , 7.32 , 7.37–7.42 , 7.50 , 7.64 , 7.80 , 7.87 , 7.90–7.96 , 8.20 , 10.46  = 65 Hz, H-11); 13C NMR  δ: 174.1 (C-1), 157.8 (C-11), 153.3 (C-16), 144.7 (C-12), 140.2 (C-3), 139.6 (1J(13C-119Sn) = 1062 Hz, C-i), 136.4 (2J(13C-117/119Sn) = 60.4, C-o), 135.6 (C-13), 134.7 (C-9), 130.5 (C-m), 129.5 (C-5), 128.9 (4J(13C-117/119Sn) = 90.5, C-p, C-7), 127.4 (C-4), 125.1 (C-15), 124.8 (C-2), 124.5 (C-14), 124.0 (C-6), 119.6 (C-8), 109.2 (C-10); 119Sn NMR  δ: −332; MS: (DART+) [m/z] (%):  (85). HR-MS (DART+) m/z: 537.06250 , observed: 537.05877.Compound 1d was prepared from 0.235 g (1.364 mmol) of 2-hydroxy-1-naphthaldehyde, 0.1503 g (1.364 mmol) of 2-amino-3-hydroxypyridine and 0.4210 g (1.364 mmol) of bis[(trimethylsilyl)methyl]tin(IV) oxide, producing 0.7156 g (95%) of a red solid; m.p. 88–90 °C; molar conductivity, ΛM : 23.6 μS cm−1; UV-Vis : 219 , 256  π → π* (aromatic), 348  π → π* (C=N), 488  n → π* (C=N); IR (ATR) cm−1: 3046 ν(C-H), 2948 νas (C-H), 2890 νsim(C-H), 1602 ν(C=O), 603 ν(Sn-C), 549 ν(Sn-O), 488 ν(Sn-N); 1H NMR  δ: 0.00 , 0.48 , 6.85 , 7.05–7.08 , 7.34 , 7.57 , 7.68 , 7.78 , 7.82 , 8.28 , 10.51  = 56 Hz, H-11); 13C NMR  δ: 172.4 (C-1), 156.5 (C-11), 151.9 (C-16), 143.7 (C-12), 138.8 (C-3), 134.2 (C-13), 133.7 (C-9), 128.3 (C-5), 127.6 (C-7), 126.0 (C-4), 123.8 (C-2), 123.5 (C-14), 123.2 (C-15), 122.6 (C-6), 118.4 (C-8), 107.6 (C-10), 7.1 (1J(13C-117/119Sn) = 519, C-α), 0.0 (C-β); 119Sn NMR  δ: −154; MS: (DART+) [m/z] (%):  (16). HR-MS (DART+) m/z: 557.11025 , observed: 557.10326.Compound 2O3·(SnO2)x)-coated glass (glass-ITO) substrates. Previously, the glass and glass-ITO substrates were sequentially washed in an ultrasonic bath with dichloromethane, methanol and acetone. The silicon substrate was washed with a p solution  to remove surface oxides. In order to obtain the quinoid form in the PEDOT:PSS polymer, the films were post-treated by exposure to isopropanol (IPA) vapor while heated at 40 °C for 10 min. For the hybrid films on Corning glass, the UV-Vis spectra were obtained in the 200–1100 nm wavelength range with a UV-Vis 300 Unicam spectrophotometer. Topographic and mechanical characteristics were investigated with an atomic force microscope (AFM) using a Ntegra platform. Finally, the devices were fabricated by using ITO as an anode and silver as a cathode: glass/ITO/organotin(IV) complex/Ag. For this evaluation, a programmable voltage source, a sensing station with lighting and a temperature-controller circuit from Next Robotix and an auto-ranging Keithley 4200-SCS-PK1 pico-ammeter were employed. The hybrid films were deposited by the spin-coating technique, and Smart Coater 200 equipment was used. The dispersion used for the manufacture of the films consisted of 6 mL of a graphene-PEDOT:PSS hybrid dispersion in dimethylformamide. Subsequently, a saturated dispersion was generated with the pentacoordinated organotin(IV) complex. The graphene-PEDOT:PSS-organotin(IV) complex mixture was dispersed with the G560 shaker of Scientific Industries Vortex-Genie. The dispersion was later deposited on the substrate, and the equipment was operated at a constant angular speed of 900 rpm for 20 s and then at an accelerated speed of 300 rpm/s and dried at 80 °C for 3 min. Thin films were deposited on glass, silicon wafers (c-Si) and indium tin oxide (In1b (cyclohexyl substituent) had the best mechanical  properties; however, the film with complex 1d ((trimethylsilyl)methyl substituent) had the best ohmic behavior, and the film with complex 1c (diphenyl substituent) had the smallest optical band gap  complexes also determines the mechanical and optical behaviors of the hybrid films.The synthesis of four pentacoordinated organotin(IV) complexes prepared by one-pot synthesis through the reaction of 2-hydroxy-1-naphthaldehyde, 2-amino-3-hydroxypyridine and organotin oxides was carried out. The organotin(IV) complexes were used to fabricate hybrid films with PEDOT:PSS and graphene, and the film with complex