4 hydroxybenzaldehyde

¹H and ¹³C NMR spectra were recorded on a Bruker Avance iii-500 spectrometer (Bruker BioSpin AG, Fällanden, Switzerland) at 298 K. The ¹H and ¹³C NMR chemical shifts were referenced with respect to residual solvent peaks (δ TMS = 0). A Shimadzu LCMS-2020 and a Bruker maXis 4G QTOF instrument (Bruker BioSpin AG, Fällanden, Switzerland) were used to record electrospray ionization (ESI) and HR-ESI mass spectra, respectively. PerkinElmer UATR Two (Perkin Elmer, 8603 Schwerzenbach, Switzerland) and Shimadzu UV2600 (Shimadzu Schweiz GmbH, 4153 Reinach, Switzerland) instruments were used to record FT-infrared (IR) and absorption spectra, respectively.
3-Acetylpyridine, 4-hydroxybenzaldehyde and 1-bromopropane were purchased from Acros Organics (Chemie Brunschwig AG, Basel, Switzerland) and were used as received. Ligands 2, 4, 5 and 6 were prepared as previously reported [11 (link),20 (link),21 (link)].

¹H, ¹³C{¹H} and 2D NMR spectra were recorded on a Bruker Avance iii-500 spectrometer (Bruker BioSpin AG, Fällanden, Switzerland) at 298 K. The ¹H and ¹³C NMR chemical shifts were referenced with respect to residual solvent peaks (δ TMS = 0). A Shimadzu LCMS-2020 instrument (Shimadzu Schweiz GmbH, 4153 Reinach, Switzerland) was used to record electrospray ionization (ESI) mass spectra. A PerkinElmer UATR Two instrument (PerkinElmer, 8603 Schwerzenbach, Switzerland) was used to record FT-infrared (IR) spectra, and Shimadzu UV2600 (Shimadzu Schweiz GmbH, 4153 Reinach, Switzerland) or Cary 5000 (Agilent Technologies AG, 4052 Basel, Switzerland) spectrophotometers were used to record absorption spectra. 3-Acetylpyridine and 4-hydroxybenzaldehyde were purchased from Acros Organics (Fisher Scientific AG, 4153 Reinach, Switzerland), rac-4-(butan-2-yloxy)benzaldehyde, 4-(2-methylpropoxy)benzaldehyde and 4-(tert-butoxy)benzaldehyde from Fluorochem (Chemie Brunschwig AG, 4052 Basel, Switzerland), 1-bromo-2-methylpropane from Sigma Aldrich (Chemie Brunschwig AG, 4052 Basel, Switzerland), and were used as received. 4′-(4-Hydroxyphenyl)-3,2′:6′,3″-terpyridine was prepared as previously described [6 (link)].

The
deuterated solvent (CDCl₃)
used for NMR spectroscopy, silica gel 60 (230–400 mesh) for
column chromatography, trifluoroacetic acid, p-chloranil,
MB, DPBF, triethylamine, benzene, acetonitrile, sodium ascorbate,
copper sulfate pentahydrate, cresyl violet, and boron trifluoride
diethyl etherate were provided by Merck. The following chemicals were
obtained from Sigma-Aldrich: ethanol, methanol tetrahydrofuran, sodium
thiosulfate, dimethyl sulfoxide, 2,4-dimethylpyrrole, N,N-dimethylformamide, acetone, dichloromethane,
iodic acid, iodine, hexane, sodium sulfate, N-bromosuccinimide, and glacial acetic acid. n-Butylamine was purchased from Alfa Aesar. The following
chemicals were obtained from Acros Organics: piperidine and 4-hydroxybenzaldehyde.
Bromo-1,8-naphthalic anhydride was purchased from TCI. Zinc phthalocyanine
and 1-azido-1-deoxy-β-d-glucopyranoside tetraacetate
were purchased from ABCR. The rest of the chemicals used in the synthesis
were of reagent grade unless otherwise specified.