Aldehydes

All glassware used was dried thoroughly in an oven, assembled hot, and cooled under a stream of dry nitrogen prior to use. All reactions and manipulations of air- and moisture-sensitive materials were carried out using standard techniques for the handling of such materials. All chemicals were commercial products of the highest purity which were further purified before use by using standard methods. HBpin, aldehydes, ketones, and alkenes were purchased from Aldrich Chemical Company, Alfa Aesar, and Tokyo Chemical Industry Company (TCI). ¹H NMR spectra were measured at 400 MHz with CDCl₃ as a solvent at ambient temperature unless otherwise indicated and the chemical shifts were recorded in parts per million downfield from tetramethylsilane (δ = 0 ppm) or based on residual CDCl₃ (δ = 7.26 ppm) as the internal standard. The coupling constants (J) are reported in hertz. Analytical thin-layer chromatography (TLC) was performed on glass precoated with silica gel (Merck, Rahway, NJ, USA, silica gel 60 F₂₅₄). Column chromatography was carried out using 70–230 mesh silica gel (Merck) at normal pressure. GC analyses were performed on a Younglin Acme 6100M and 6500 GC FID chromatography, using an HP-5 capillary column (30 m). All GC yields were determined with the use of naphthalene as the internal standard and the authentic sample.

Commercially available reagents were used
without further purification. Aldehydes, malonic acid, piperidine,
and all other reagents were purchased from Sigma-Aldrich (St Louis,
MO) AlfaAesar, or Fisher Scientific. Restriction enzymes, T4 polynucleotide
kinase, T4 DNA ligase, Q5 high-fidelity DNA polymerase, and broad
range protein marker (12–250 kDa) were purchased from New England
Biolabs (Ipswich, MA). Escherichia coli DH5α
and BL21 (DE3) cells were purchased from New England
Biolabs (Ipswich, MA). Expression vector pET-28b was purchased from
Novagen (Darmstadt, Germany) and was used for gene expression. HPLC
filter vials 0.45uM PVDF with a pre-slit cap were bought from Thomson
(California, USA). LB broth base including trace elements was supplied
by Formedium (Norfolk, UK). Synthesized oligonucleotides were purchased
from Eurofins Genomics (Ebersberg, Germany).

Aldehydes, triazine, benzene-1,3-disulfonyl chloride, 2-aminopyridine, malononitrile, chlorosulfonic acid, and solvents were purchased from Sigma-Aldrich Company. Also, the thin-layer chromatography (TLC) of the commercial plates (silica gel 60 F254), were purchased from Merck Company. FT-IR spectra were recorded in a spectrophotometer (PerkinElmer 781). To investigate the surface morphology of the catalyst FE-SEM images and EDX analyses provided by a Sigma ZEISS, Oxford Instruments Field Emission Scanning Electron Microscope. The morphology of prepared catalysts was investigated using TEM by a Philips CM 120, Netherlands and microscope with an accelerating voltage of 150 kV. X-ray diffraction was performed using a Philips X'pert MPD diffractometer with a Cu operating at a current of 100 mA and a voltage of 45 kV, with the Cu-Kα radiation (λ = 0.154056 nm) at the 2q range of 10–80 and scanning at the speed of 0.05° per minute. Thermogravimetric analysis (TGA) was carried out using Shimadzu DTG-60 instrument at 25 to 600 °C. The pore volume and pore size distribution were resulted from the desorption profiles of the isotherms using the Barrett–Joyner–Halenda (BJH) method. NMR spectra (Bruker 400 MHz) were used to confirm product structure by DMSO-d6 as a solvent on a Bruker DRX-400 spectrometer.