This readme file was generated on 2023-11-17 by Jesse Hsu GENERAL INFORMATION Dataset title: Compound data for Selective Electrocatalytic Degradation of Ether-Containing Polymers Contributor: Jesse H. Hsu Affiliation: Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States ORCID: 0000-0002-6979-3008 Contributor: Brett P. Fors Affiliation: Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States ORCID: 0000-0002-2222-3825 Associated Article: Hsu, J. H.; Ball, T. E.; Oh, S.; Stache, E. E.; Fors, B. P. Angew. Chem. Int. Ed. 2023, e202316578. Funding: This work was supported by the NSF under award number CHE-2203758. This work made use of the Cornell Center for Materials Research Shared Facilities that are supported by the NSF MRSEC program (DMR1719875), and the NMR facility, which is supported, in part, by the NSF through MRI award CHE-1531632. Licensing: The dataset is distributed under a CC BY 4.0 License https://creativecommons.org/licenses/by/4.0/. Cite the dataset as: Hsu, J. H.; Ball, T. E; Oh, S.; Stache, E. E.; Fors, B. P. (2023) Compound data for Selective Electrocatalytic Degradation of Ether-Containing Polymers. [Dataset] Cornell University eCommons Repository. https://doi.org/10.7298/e8d7-bh51 DATASET OVERVIEW Dataset title: Compound data for Selective Electrocatalytic Degradation of Ether-Containing Polymers Description: Characterization data included for the associated article and Supporting Information. Data types include NMR, GPC, CV, and FT-IR. Experimental detail included in the Supporting Information. Date of data collection: 2022-02-09 - 2023-10-21 File formats and software: .xlsx .csv .mnova .JCAMP XLSX files: proprietary spreadsheet file format from Microsoft Excel. CSV files: for preservation purposes, and long-term access, text-based, comma-separated variable versions are included of all Microsoft Excel files. MNOVA files: proprietary spectra data file format from Mestralab JCAMP files: text-based open file format standard for spectra data from IUPAC (International Union of Pure and Applied Chemistry); can be opened as text, and data processable by most spectra viewing and analysis programs. For preservation purposes, and long-term access, text based .jcamp versions are included of all .mnova files. Compound identifiers: IUPAC Name, InChI, InChIKey IUPAC Name: standard nomenclature from the International Union of Pure and Applied Chemistry (IUPAC) InChI: International Chemical Identifier, machine-readable identifier from IUPAC InChIKey: hash-code of InChI for indexing, from IUPAC DATA FILES Supporting Information: File Name: JHH_SupportingInformation_Electrodegradation.pdf Description: Document which organizes and decribes all supplementary experiments NMR data: File Name: JHH_S05_benzanilide Compound Name: benzanilide Experiment Description: 1H NMR spectrum of benzanilide. Taken in acetone-d6. File Name: JHH_S07_PEVE Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: 1H NMR spectrum of PEVE. Taken in chloroform-d. File Name: JHH_S08_PMMA Compound Name: poly(methyl methacrylate) (PMMA) Experiment Description: 1H NMR spectrum of PMMA. Taken in chloroform-d. File Name: JHH_S10_PMA Compound Name: poly(methyl acrylate) (PMA) Experiment Description: 1H NMR spectrum of PMA. Taken in chloroform-d. File Name: JHH_S11_PMA-PDHF-copolymer-1H Compound Name: poly(methyl acrylate-co-2,3-dihydrofuran) (poly(MA-co-DHF)) Experiment Description: 1H NMR spectrum of poly(MA-co-DHF). Taken in chloroform-d. File Name: JHH_S12_PMA-PDHF-copolymer-13C Compound Name: poly(methyl acrylate-co-2,3-dihydrofuran) (poly(MA-co-DHF)) Experiment Description: 13C NMR spectrum of poly(MA-co-DHF). Taken in chloroform-d. File Name: JHH_S13_PU Compound Name: poly(propylene oxide)-based polyurethane (PU) Experiment Description: 1H NMR spectrum of PU. Taken in chloroform-d. File Name: JHH_S15_PDHF Compound Name: poly(2,3-dihydrofuran) (PDHF) Experiment Description: 1H NMR spectrum of PDHF. Taken in chloroform-d. File Name: JHH_S16_iPPO Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 1H NMR spectrum of iPPO. Taken in chloroform-d. File Name: JHH_S17_PVAc Compound Name: poly(vinyl acetate) (PVAc) Experiment Description: 1H NMR spectrum of PVAc. Taken in chloroform-d. File Name: JHH_S26_PDHF-partially-degraded-isolated Compound Name: poly(2,3-dihydrofuran) (PDHF) Experiment Description: 1H NMR spectra of PDHF before and after 20 min of electrolytic degradation in dichloromethane followed by two precipitations in methanol. Taken in chloroform-d. File Name: JHH_S27_PDHF-degradation-DCM Compound Name: poly(2,3-dihydrofuran) (PDHF) Experiment Description: 1H NMR spectra of the PDHF crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane. Taken in chloroform-d. File Name: JHH_S29_PDHF-degradation-DCM-solid Compound Name: poly(2,3-dihydrofuran) (PDHF) Experiment Description: 1H NMR spectrum of the solid produced after the electrolytic degradation of PDHF for 25 h in dichloromethane. Taken in dimethyl sulfoxide-d6. File Name: JHH_S30_PDHF-degradation-DMSO Compound Name: poly(2,3-dihydrofuran) (PDHF) Experiment Description: 1H NMR spectra of the PDHF crude reaction mixture before and after 20 h of electrolytic degradation in a CDCl3/DMSO-d6 (1:1) solvent mixture. Taken in dimethyl sulfoxide (DMSO)-d6. File Name: JHH_S33_PEVE-degradation Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: 1H NMR spectra of the PEVE crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane. Taken in chloroform-d. File Name: JHH_S34_PEVE-degradation-spiking-experiments Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: 1H NMR spectra of the PEVE crude reaction mixture after 25 h of electrolytic degradation in dichloromethane, after spiking the NMR sample with a small amount of acetic acid, and after spiking with a small amount of acetaldehyde. Taken in chloroform-d. File Name: JHH_S35_iPPO-degradation Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 1H NMR spectra of the iPPO crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane. Taken in chloroform-d. File Name: JHH_S36_iPPO-degradation-spiking-experiments Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 1H NMR spectra of the iPPO crude reaction mixture after 25 h of electrolytic degradation, after spiking the NMR sample with a small amount of formic acid, after spiking with a small amount of acetic acid, and after spiking with a small amount of acetaldehyde. Taken in chloroform-d. File Name: JHH_S37_iPPO-degradation-kinetics Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 1H NMR spectra of the iPPO crude reaction mixture before and after 2 h, 6 h, 14 h, 25 h, 48 h, and 72 h of electrolytic degradation in dichloromethane, performed in triplicate. Taken in chloroform-d. File Name: JHH_S38_iPPO-degradation-CDCl3 Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 1H NMR spectra of the iPPO crude reaction mixture before and after 25 h of electrolytic degradation in chloroform-d. Taken in chloroform-d. File Name: JHH_S39-S40_iPPO-degradation-CDCl3-COSY Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: COSY-NMR spectra of the iPPO crude reaction mixture before and after electrolytic degradation in chloroform-d. Taken in chloroform-d. File Name: JHH_S41_iPPO-degradation-CDCl3-13CNMR Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 13C NMR spectra of the iPPO crude reaction mixture before and after 25 h of electrolytic degradation in chloroform-d. Taken in chloroform-d. File Name: JHH_S42-S43_iPPO-degradation-CDCl3-HSQC Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: HSQC-NMR spectra of the iPPO crude reaction mixture before and after 25 h of electrolytic degradation in chloroform-d. Taken in chloroform-d. File Name: JHH_S44-S45_iPPO-degradation-CDCl3-HMBC Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: HMBC-NMR spectra of the iPPO crude reaction mixture before and after 25 h of electrolytic degradation in chloroform-d. Taken in chloroform-d. File Name: JHH_S46_iPPO-degradation-20percNHPI Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 1H NMR spectra of the iPPO crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane using a catalytic amount (20 mol%) of NHPI. Taken in chloroform-d. File Name: JHH_S47_iPPO-degradation-10percNHPI Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 1H NMR spectra of the iPPO crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane using a catalytic amount (10 mol%) of NHPI. Taken in chloroform-d. File Name: JHH_S48_iPPO-degradation-5percNHPI Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 1H NMR spectra of the iPPO crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane using a catalytic amount (5 mol%) of NHPI. Taken in chloroform-d. File Name: JHH_S49_iPPO-degradation-double-polymer Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: 1H NMR spectra of the iPPO crude reaction mixture before and after electrolytic degradation in dichloromethane using a doubled loading of iPPO (0.025 g, 0.42 mmol, 1.0 equiv), doubled reaction time (50 h), and a catalytic amount of NHPI (10 mol%, 0.0070 g, 0.043 mmol, 0.10 equiv). Taken in chloroform-d. File Name: JHH_S50_PU-degradation Compound Name: poly(propylene oxide)-based polyurethane (PU) Experiment Description: 1H NMR spectra of the PU crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane using a catalytic amount (20 mol%) of NHPI. Taken in chloroform-d. File Name: JHH_S51_PU-degradation-synthesized-foam Compound Name: poly(propylene oxide)-based polyurethane (PU) foam Experiment Description: 1H NMR spectra of the synthesized PU foam crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane using a catalytic amount (20 mol%) of NHPI. Taken in chloroform-d. File Name: JHH_S52_PU-degradation-commercial-foam Compound Name: commercial polyurethane (PU) foam Experiment Description: 1H NMR spectra of the commercial PU foam crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane using a catalytic amount (20 mol%) of NHPI. Taken in chloroform-d. File Name: JHH_S54_MeTHF-oxidation Compound Name: 2-methyltetrahydrofuran (MeTHF) Experiment Description: 1H NMR spectra of the MeTHF crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane. Taken in chloroform-d. File Name: JHH_S55-S57_MeTHF-oxidation-COSY Compound Name: 2-methyltetrahydrofuran (MeTHF) Experiment Description: COSY-NMR spectra of the MeTHF crude reaction mixture before and after 25 h of electrolytic degradation in dichloromethane. Taken in chloroform-d. File Name: JHH_S58_MeTHF-oxidation-spiking-experiments Compound Name: 2-methyltetrahydrofuran (MeTHF) Experiment Description: 1H NMR spectra of the MeTHF crude reaction mixture after 25 h of electrolytic degradation and after spiking the NMR sample with a small amount of gamma-valerolactone. Taken in chloroform-d. GPC data: File Name: JHH_S06_PEVE_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under our standard degradation conditions for 15 min, 30 min, 60 min, 120 min, and 180 min. File Name: JHH_S08_PMMA_GPC Compound Name: poly(methyl methacrylate) (PMMA) Experiment Description: GPC traces of PMMA before and after electrolytic degradation under our standard degradation conditions for 24 h. File Name: JHH_S09_PMA_GPC Compound Name: poly(methyl acrylate) (PMA) Experiment Description: GPC traces of PMA before and after electrolytic degradation under our standard degradation conditions for 24 h. File Name: JHH_S13_PU_GPC Compound Name: poly(propylene oxide)-based polyurethane (PU) Experiment Description: GPC traces of the poly(propylene oxide) polyol used to synthesize PU, and PU before and after electrolytic degradation in ethyl acetate solvent with a catalytic amount (20 mol%) of NHPI mediator for 30 min, 60 min, 120 min, 240 min, 360 min and 25 h. File Name: JHH_S15_PDHF_GPC Compound Name: poly(2,3-dihydrofuran) (PDHF) Experiment Description: GPC traces of PDHF before and after electrolytic degradation under our standard degradation conditions for 2 min, 5 min, 7 min, and 10 min. File Name: JHH_S16_iPPO_GPC Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: GPC traces of iPPO before and after electrolytic degradation under our standard degradation conditions for 10 min, 20 min, 30 min, 60 min, and 120 min. File Name: JHH_S17_PVAc_GPC Compound Name: poly(vinyl acetate) (PVAc) Experiment Description: GPC traces of PVAc before and after electrolytic degradation under our standard degradation conditions for 24 h. File Name: JHH_S19_1mA-1h_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation with 1.0 mA of electrochemical current for 1 h. File Name: JHH_S19_HFIP-additive_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation with hexafluoro-2-isopropanol (HFIP) in place of acetic acid (AcOH) for 2 h. File Name: JHH_S19_hydroxyacetone-additive_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation with hydroxyacetone in place of acetic acid (AcOH) for 2 h. File Name: JHH_S19_platinum-cathode_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation with a platinum cathode in place of stainless steel for 2 h. File Name: JHH_S19_point2mA-10h_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation with 0.2 mA of electrochemical current for 10 h. File Name: JHH_S19_TBAP-electrolyte_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation with tetrabutylammonium perchlorate (TBAP) in place of tetrabutylammonium tetrafluoroborate (TBABF4) for 2 h. File Name: JHH_S19_tert-butanol-additive_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation with tert-butanol (tBuOH) in place of acetic acid (AcOH) for 2 h. File Name: JHH_S19_tetrachloro-NHPI_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation with N-hydroxytetrachlorophthalimide (tetrachloro-NHPI) in place of N-hydroxyphthalimide (NHPI) for 2 h. File Name: JHH_S19_TFA-additive_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation with trifluoroacetic acid (TFA) in place of acetic acid (AcOH) for 2 h. File Name: JHH_S21a_benzanilide-mediator_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air with benzanilide in place of N-hydroxyphthalimide (NHPI) for 60 min, 120 min, and 180 min. File Name: JHH_S21a_DABCO-mediator_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air with 1,4-diazabicyclo[2.2.2]octane (DABCO) in place of N-hydroxyphthalimide (NHPI) for 60 min, 120 min, and 180 min. File Name: JHH_S21a_HOBt-mediator_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air with hydroxybenzotriazole (HOBt) in place of N-hydroxyphthalimide (NHPI) for 30 min, 70 min, 120 min, and 180 min. File Name: JHH_S21a_NHPI-mediator_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air with N-hydroxyphthalimide (NHPI) in place of N-hydroxyphthalimide (NHPI) for 15 min, 30 min, 60 min, 120 min, and 180 min. File Name: JHH_S21a_NMO-mediator_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air with N-methylmorpholine N-oxide (NMO) in place of N-hydroxyphthalimide (NHPI) for 30 min, 60 min, 120 min, and 180 min. File Name: JHH_S21a_no-mediator_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air with no mediator for 15 min, 30 min, 60 min, 120 min, and 180 min. File Name: JHH_S21a_quinuclidine-mediator_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air with quinuclidine in place of N-hydroxyphthalimide (NHPI) for 60 min, 120 min, and 180 min. File Name: JHH_S21a_TEMPO-mediator_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air with 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) in place of N-hydroxyphthalimide (NHPI) for 60 min, 120 min, and 180 min. File Name: JHH_S21c_argon_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under argon for 15 min, 30 min, 60 min, 120 min, and 180 min. File Name: JHH_S21c_open-to-air_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air for 15 min, 30 min, 60 min, 120 min, and 180 min. File Name: JHH_S21c_oxygen_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under oxygen for 15 min, 30 min, 60 min, 120 min, and 180 min. File Name: JHH_S22_PEVE-ONOFF_GPC Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: GPC traces of PEVE before and after electrolytic degradation under air while turning the electrochemical current ON or OFF after specified times. File Name: JHH_S23_PMA-PDHF-blend_GPC Compound Name: blend of poly(methyl acrylate) (PMA) and poly(2,3-dihydrofuran) (PDHF) Experiment Description: GPC traces of the PMA and PDHF blended sample before and after electrolytic degradation under our standard degradation conditions for 30 min. File Name: JHH_S23_PMA-PDHF-copolymer_GPC Compound Name: poly(methyl acrylate-co-2,3-dihydrofuran) (poly(MA-co-DHF)) Experiment Description: GPC traces of poly(MA-co-DHF) before and after electrolytic degradation under our standard degradation conditions for 24 h. File Name: JHH_S23_PMMA-iPPO-blend_GPC Compound Name: blend of poly(methyl methacrylate) (PMMA) and isotactic poly(propylene oxide) (iPPO) Experiment Description: GPC traces of the PMMA and iPPO blended sample before and after electrolytic degradation under our standard degradation conditions for 24 h. File Name: JHH_S25_PDHF-ONOFF_GPC Compound Name: poly(2,3-dihydrofuran) (PDHF) Experiment Description: GPC traces of PDHF before and after electrolytic degradation under air while turning the electrochemical current ON or OFF after specified times. CV data: File Name: JHH_S70_benzanilide_CV Compound Name: benzanilide Experiment Description: Cyclic voltammogram of benzanilide (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S70_DABCO_CV Compound Name: 1,4-diazabicyclo[2.2.2]octane (DABCO) Experiment Description: Cyclic voltammogram of DABCO (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S70_quinuclidine_CV Compound Name: quinuclidine Experiment Description: Cyclic voltammogram of quinuclidine (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S71_benzanilide-with-pyridine_CV Compound Name: benzanilide with pyridine Experiment Description: Cyclic voltammogram of benzanilide (1.0 mM) and pyridine (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S71_NMO_CV Compound Name: N-methylmorpholine N-oxide (NMO) Experiment Description: Cyclic voltammogram of NMO (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S71_TEMPO_CV Compound Name: 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) Experiment Description: Cyclic voltammogram of TEMPO (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S72_HOBt_CV Compound Name: hydroxybenzotriazole (HOBt) Experiment Description: Cyclic voltammogram of HOBt (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S72_NHPI-with-pyridine_CV Compound Name: N-hydroxyphthalimide (NHPI) with pyridine Experiment Description: Cyclic voltammogram of NHPI (1.0 mM) and pyridine (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S72_NHPI_CV Compound Name: N-hydroxyphthalimide (NHPI) Experiment Description: Cyclic voltammogram of NHPI (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S73_HOBt-with-pyridine_CV Compound Name: hydroxybenzotriazole (HOBt) with pyridine Experiment Description: Cyclic voltammogram of HOBt (1.0 mM) and pyridine (1.0 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S73_iPPO_CV Compound Name: isotactic poly(propylene oxide) (iPPO) Experiment Description: Cyclic voltammograms of iPPO (0 mM, 1 mM, 5 mM, and 10 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S73_PEVE_CV Compound Name: poly(ethyl vinyl ether) (PEVE) Experiment Description: Cyclic voltammograms of PEVE (0 mM, 1 mM, 5 mM, and 10 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. File Name: JHH_S74_PDHF_CV Compound Name: poly(2,3-dihydrofuran) (PDHF) Experiment Description: Cyclic voltammograms of PDHF (0 mM, 1 mM, 5 mM, and 10 mM) in 0.1 M tetrabutylammonium tetrafluoroborate in dichloromethane. Scan rate 100 mV/s. Anodic sweep. FT-IR data: File Name: JHH_S75_iPPO_FT-IR Compound Name: isotactic poly(propylene oxide) Experiment Description: FT-IR spectra of the isotactic poly(propylene oxide) (iPPO) crude reaction mixture before and after 25 h of electrolytic degradation. Compound Identifiers Compound Name: benzanilide IUPAC Name: N-phenylbenzamide InChI: InChI=1S/C13H11NO/c15-13(11-7-3-1-4-8-11)14-12-9-5-2-6-10-12/h1-10H,(H,14,15) InChIKey: ZVSKZLHKADLHSD-UHFFFAOYSA-N Schema Number: S05, S70, S71 Compound Name: poly(ethyl vinyl ether) (PEVE) IUPAC Name: ethenoxyethane (monomer) InChI: InChI=1S/C4H8O/c1-3-5-4-2/h3H,1,4H2,2H3 InChIKey: FJKIXWOMBXYWOQ-UHFFFAOYSA-N Schema Number: S06, S07, S19, S21a, S21c, S22, S33, S34, S73, Compound Name: poly(methyl methacrylate) (PMMA) IUPAC Name: methyl 2-methylprop-2-enoate (monomer) InChI: InChI=1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3 InChIKey: VVQNEPGJFQJSBK-UHFFFAOYSA-N Schema Number: S08, S23 Compound Name: poly(methyl acrylate) (PMA) IUPAC Name: methyl prop-2-enoate (monomer) InChI: InChI=1S/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3 InChIKey: BAPJBEWLBFYGME-UHFFFAOYSA-N Schema Number: S09, S10, S11, S12, S23 Compound Name: poly(propylene oxide)-based polyurethane (PU) IUPAC Name: 2-methyloxirane (monomer) InChI: InChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3 InChIKey: GOOHAUXETOMSMM-UHFFFAOYSA-N Schema Number: S13, S50, S51, S52 Compound Name: poly(2,3-dihydrofuran) (PDHF) IUPAC Name: 2,3-dihydrofuran (monomer) InChI: InChI=1S/C4H6O/c1-2-4-5-3-1/h1,3H,2,4H2 InChIKey: JKTCBAGSMQIFNL-UHFFFAOYSA-N Schema Number: S11, S12, S15, S23, S25, S26, S27, S29, S30, S74 Compound Name: isotactic poly(propylene oxide) (iPPO) IUPAC Name: 2-methyloxirane (monomer) InChI: InChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3 InChIKey: GOOHAUXETOMSMM-UHFFFAOYSA-N Schema Number: S16, S23, S35, S36, S37, S38, S39, S40, S41, S42, S43, S44, S45, S46, S47, S48, S49, S73, S75 Compound Name: poly(vinyl acetate) (PVAc) IUPAC Name: ethenyl acetate (monomer) InChI: InChI=1S/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3 InChIKey: XTXRWKRVRITETP-UHFFFAOYSA-N Schema Number: S17 Compound Name: 2-methyltetrahydrofuran (MeTHF) IUPAC Name: 2-methyloxolane InChI: InChI=1S/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3 InChIKey: JWUJQDFVADABEY-UHFFFAOYSA-N Schema Number: S54, S55, S56, S57, S58 Compound Name: 1,4-diazabicyclo[2.2.2]octane (DABCO) IUPAC Name: 1,4-diazabicyclo[2.2.2]octane InChI: InChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2 InChIKey: IMNIMPAHZVJRPE-UHFFFAOYSA-N Schema Number: S21a, S70 Compound Name: quinuclidine IUPAC Name: 1-azabicyclo[2.2.2]octane InChI: InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2 InChIKey: SBYHFKPVCBCYGV-UHFFFAOYSA-N Schema Number: S21a, S70 Compound Name: pyridine IUPAC Name: pyridine InChI: InChI=1S/C5H5N/c1-2-4-6-5-3-1/h1-5H InChIKey: JUJWROOIHBZHMG-UHFFFAOYSA-N Schema Number: S71, S72, S73 Compound Name: N-methylmorpholine N-oxide (NMO) IUPAC Name: 4-methyl-4-oxidomorpholin-4-ium InChI: InChI=1S/2C5H11NO2/c2*1-6(7)2-4-8-5-3-6/h2*2-5H2,1H3 InChIKey: PPHSPCADBRQUKM-UHFFFAOYSA-N Schema Number: S21a, S71 Compound Name: 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) IUPAC Name: (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl InChI: InChI=1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3 InChIKey: UZFMOKQJFYMBGY-UHFFFAOYSA-N Schema Number: S21a, S71 Compound Name: hydroxybenzotriazole (HOBt) IUPAC Name: 1-hydroxybenzotriazole InChI: InChI=1S/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H InChIKey: ASOKPJOREAFHNY-UHFFFAOYSA-N Schema Number: S21a, S72, S73 Compound Name: N-hydroxyphthalimide (NHPI) IUPAC Name: 2-hydroxyisoindole-1,3-dione InChI: InChI=1S/C8H5NO3/c10-7-5-3-1-2-4-6(5)8(11)9(7)12/h1-4,12H InChIKey: CFMZSMGAMPBRBE-UHFFFAOYSA-N Schema Number: S13, S19, S21a, S46, S47, S48, S49, S50, S51, S52, S72