Supporting informationContents:1-General experimental information (Pages 1-13) 2-1 H NMR and 13 C NMR spectra of N-benzyl-4-aryl tetrahydroquinolines 3a-3p, 3-1 H NMR and 13 C NMR spectra of 4-aryl tetrahydroquinolines 3a-3l, (Pages 11-41) 4-Single crystal X-Ray diffraction data for N-benzyl-4-aryl-3-methyl tetrahydroquinoline 6d General Experimental InformationAll reagents were purchased from Merck, J.T. Baker and Sigma and Aldrich Chemical Co. and used without further purification. The reaction progress was monitored using thin layer chromatography on PF254 TLC aluminum sheets from Merck. Column chromatography was performed using Silica gel (60-120 mesh). The melting points (uncorrected) were determined using a Fisher-Johns melting point apparatus. IR spectra were recorded on a FTIR Bruker Tensor 27 spectrophotometer coupled to a Bruker platinum ATR cell. Mass spectra were recorded on an ESI-IT Amazon X (Bruker Daltonics) with direct injection, operating in Full Scan mode at 300°C and 4500V in the capillary, using nitrogen as nebulizer gas with an influx of 8 L/min and 30 psi.NMR spectra ( 1 H and 13 C) were measured on a Bruker Ultrashield-400 spectrometer (400 MHz 1 H NMR and 100 MHz 13 C NMR), using CDCl 3 as solvent and reference. J values are reported in Hz; chemical shifts are reported in ppm (δ) relative to the solvent peak (residual CHCl 3 in CDCl 3 at 7.26 ppm for protons). Signals were designated as follows: s, singlet; d, doublet; dd, doublet of doublets; ddd, doublet of doublets of doublets; t, triplet; td, triplet of doublets; q, quartet; m, multiplet; br., broad.General procedure for the synthesis of N-benzyl-4-aryl tetrahydroquinolines: All the reactions were performed at room temperature unless otherwise stated. In a round bottom flask, a 5 mL solution in anhydrous acetonitrile of Nbenzylaniline (1 mmol) and formaldehyde (37% in methanol) (1.1 mmol) was prepared and stirred for 10 minutes. A 5 mL solution of HCl 2N (1.1 mmol) in MeCN was then added and after stirring for 20 minutes, the dienophile (trans-anethole or isoeugenol) (1.1 mmol) was incorporated to the reaction mixture and was vigorously stirred. The reaction achieved completion within 2-21 hours (monitored by TLC). The mixture was poured into a saturated solution of NaHCO 3 (15 mL), extracted with ethyl acetate (3 x 15 mL) and dried over Na 2 SO 4 . The crude product

A novel and highly efficient synthetic approach for the expedite construction of new octahydroacridine-isoxazole- and octahydroacridine-1,2,3-triazole-based molecular hybrids is first reported. Rapid access to the octahydroacridine core was achieved in a highly diastereoselective fashion via cationic Povarov reaction of N-propargyl anilines and citronella essential oil (Cymbopogon nardus). The subsequent 1,3-dipolar and Cu (I) catalyzed alkyne-azide cycloaddition reaction of the terminal alkyne fragment with the corresponding oxime or azide affords the desired 3,5-isoxazoles and 1,2,3-triazoles, respectively, as interesting molecular hybrid models for pharmacological studies.

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The chemical immobilization of a dibenzoic acid oligo (phenylene vinylene) (OPV) derivative for TiO2 sensitization was evaluated as a strategy to enhance both the stability and photocatalytic performance of this π‐conjugated moiety when applied to the photodegradation of indigo carmine dye (IC) as model pollutant. The results show that the electron injection from the photoexcited OPV to the TiO2 conduction band remarkably boosts the IC degradation ability under visible light illumination. The use of SiO2 as non‐photoactive support was also investigated to simultaneously determine the role of the inorganic support in the photocatalytic process. The spectroscopic, thermal, and surface characterization validated the successful grafting of the OPV to the inorganic supports. Moreover, superoxide radical and singlet oxygen were established as the active species involved in the dye degradation identifying an additional direct reducing pathway. Interestingly, the use of electron donors proved to be an ineffective approach to increase the system performance, entailing that the OPV regeneration proceeds chiefly via back electron transfer processes. Finally, the reusability tests confirmed that TiO2/OPV material retains up to 86 % of their photocatalytic activity during the first five cycles, demonstrating a critical enhancement in the organic conjugated framework stability.

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