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4 protocols using m 560 apparatus

1

Structural Elucidation of Compounds

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1H- (400, 500, and 600 MHz), and 13C-NMR (100, 125, and 150 MHz) and 2D-NMR spectra were recorded on Bruker Avance-NMR spectrometers (France) in CD3OD, CD3COCD3 or DMSO-d6. Melting points were recorded on Buchi M-560 apparatus (Japan). EI- and HREI-MS were recorded on JEOL JMS-600H (Japan). Optical rotations of all isolated compounds were measured on JASCO P-2000 polarimeter (Japan) in chloroform or methanol. IR analyses were performed on Bruker Vector 22 FT-IR spectrometer (France). Evolution 300 UV-visible spectrophotometer was used to record the UV spectra (Thermo Scientific, England). Single-crystal X-ray diffraction data was collected on Bruker APEXII D8 Venture diffractometer, fitted with PHOTON 100 detector (CMOS technology), and fine-focus sealed tube having X-ray source [Cu Kα radiation α = 1.54178 Å]. Reflection intensities were integrated using SAINT software. Absorption correction was done on M-multi-scan. Structures were solved on SHELXTL [30 –31 ].
Crystallographic data for compounds 1, 2, 4, and 8 were deposited with the Cambridge Crystallographic Data Center and can be obtained free of charge from the Cambridge Crystallographic Data Center viawww.ccdc.cam.ac.uk/data_request/cif.
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2

Spectroscopic Characterization of Synthesized Compounds

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IR spectra were recorded on an IR Affinity-1 Fourier transform spectrometer for studies in the mid-IR range in KBr pellets. 1H and 13C NMR spectra (400 and 101 MHz, respectively) were acquired on a Bruker Avance III HD 400 NanoBay spectrometer in DMSO-d6, using the signals of the deuterated solvent DMSO-d6 as internal standard (the NMR spectra of the synthesized compounds are depicted in Supplementary Materials). High resolution mass spectra (electrospray ionization) were performed on a Shimadzu Nexera X2 LCMS-9030 liquid hybrid quadrupole time-of-flight mass spectrometer and Bruker micrOTOF. High performance liquid chromatography–high resolution mass spectrometry (HPLC-MS-HR) results were obtained on a Prominence LC-20 HPLC system (Shimadzu, Japan) in combination with an LTQ Orbitrap XL mass spectrometer (Thermo Fisher Scientific, Waltham, MA, USA) using electrospray ionization. Melting points were determined on a Büchi M-560 apparatus with a heating rate of 1 °C/min in the melting range. Monitoring of the reaction progress was done by TLC on Merck Kieselgel 60 F254 plates. Analytical grade solvents were used without additional purification.
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3

Characterization of Organic Polymers

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Melting points were measured by a Büchi M-560 apparatus. HRMS spectra were recorded on a Bruker ESI microTOF II instrument. 1H, 13C, 2D-COSY, and -HMQC NMR spectra (400 or 100 MHz) were measured in CDCl3 containing tetramethylsilane (TMS) as an internal standard with an ECX400 NMR spectrometer. UV/vis spectra were measured in a quartz cell (1 cm path length) by recording on a JASCO V-650 spectrometer equipped with an ETCS-761 temperature controller. Fluorescence spectra were measured in the same cell using a JASCO FP-8500 spectrophotometer equipped with an ETC-815 temperature controller. Fluorescence lifetime decays were observed in the same cell by a Hamamatsu Quantaurus-Tau single-photon-counting instrument fitted with an LED excitation light (340 nm). IR spectra were measured on a JASCO FT/IR-4700 spectrometer. The molecular weights of the PTs were determined using polystyrene standards through an analytical GPC with a TOSOH TSKgel α-4000 column (condition: 40 °C, 0.5 mL min−1, DMF).
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4

Synthetic Methodology for Iodonium Salts

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All reagents and solvents were obtained from commercial sources and used without further purification. Iodonium salts were obtained using the previously reported procedure [1 (link)]. Melting points were measured on a BUCHI M-560 apparatus (BUCHI Labortechnik AG, Flawil, St. Gallen, Switzerland) in capillaries and were not corrected. The NMR spectra were recorded on Bruker Avance III HD (400 MHz) (Bruker Corp., Billerica, MA, USA). The 1H NMR spectra were recorded at 400 MHz and the 13C NMR spectra were recorded at 100 MHz. Chemical shifts were reported in parts per million (ppm). The 1H and 13C chemical shifts were referenced relative to the residual solvent signal. High-resolution mass spectra (HRMS) were recorded using electrospray ionization (ESI) methods on a Bruker micrOTOF spectrometer (Bruker Corp., Billerica, MA, USA) equipped with an ESI source. Elemental CHNS analysis was obtained on an elemental analyzer Thermo Flash EA 2000 (Thermo Fisher Scientific, Rockford, IL, USA), and sulfanilamide was used as a standard. Drying of the samples for elemental analysis was carried out at 80 °C to constant weight in a dry argon atmosphere using combined TG-DSC analysis on an SDT Q600 thermal analyzer (TA Instruments New Castle, DE, USA).
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