Compound characterization data — Wei et al., 2026

Yiting Wei, Anne Germann, Shihao Ding, Jiaheng Liu, Weixiu Zhong, Jan Meisner, Yun Liu. “Versatile bimolecular mechanochemistry via heterobicyclic mechanophores.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007816/v1

3
TLC Rf (10:1 petroleum ether : EtOAc, 254 nm UV)	0.52
¹H NMR (400 MHz, CDCl₃)	δ = 5.88–5.73 (m, 1H), 5.17–5.03 (m, 2H), 4.22 (t, J = 6.8 Hz, 2H), 2.65 (s, 2H), 2.43 (dt, J = 6.8, 1.4 Hz, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ = 161.21, 142.46, 133.74, 117.38, 63.91, 32.96, 27.10
HR-ESI-MS	C₁₄H₁₉O₄ [M+H]⁺, Calculated: 251.1278; Found: 251.1278

4
TLC Rf (10:1 petroleum ether : EtOAc, 254 nm UV)	0.44
¹H NMR (400 MHz, CDCl₃)	δ 5.58 (td, J = 5.1, 2.5 Hz, 0.8H, Z-isomer), 5.36 (dd, J = 4.9, 3.1 Hz, 0.2H, E-isomer), 4.31–4.19 (m, 2H), 2.68 (s, 0.4H, E-isomer), 2.66 (s, 1.6H, Z-isomer), 2.53–2.38 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 162.66, 161.88, 141.80, 140.23, 129.62, 128.95, 63.77, 62.82, 32.33, 27.24, 26.74, 26.62
HR-ESI-MS	C₁₂H₁₄NaO₄ [M+Na]⁺, Calculated: 245.0784; Found: 245.0785
¹H and ¹³C NMR spectra	Image data were not transcribed

M1
TLC Rf (4:1 petroleum ether : EtOAc, KMnO₄)	0.49
¹H NMR (400 MHz, CDCl₃)	δ = 5.53–5.36 (m, 2H), 4.79 (td, J = 10.5, 2.4 Hz, 2H), 4.03–3.88 (m, 2H), 2.72–2.52 (m, 4H), 2.25–2.09 (m, 2H), 1.95–1.84 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ = 165.10, 128.63, 64.08, 63.85, 27.13, 25.28
HR-ESI-MS	C₁₂H₁₅O₅ [M+H]⁺, Calculated: 239.0914; Found: 239.0914
Single-crystal XRD, empirical formula	C₁₂H₁₄O₅
Single-crystal XRD, formula mass	238.23 g mol⁻¹
Single-crystal XRD (180 K, λ = 1.54184 Å), crystal system and space group	monoclinic; P2₁
Single-crystal XRD, unit cell	a = 5.6024(2) Å, α = 90°; b = 13.9821(6) Å, β = 90.533(4)°; c = 7.2982(3) Å, γ = 90°; V = 571.67(4) Å³; Z = 2
Single-crystal XRD, calculated density	1.384 Mg m⁻³
Single-crystal XRD, absorption coefficient and F(000)	0.912 mm⁻¹; 252.0
Single-crystal XRD, crystal size	0.23 × 0.07 × 0.04 mm³
Single-crystal XRD, data collection	θ = 3.161 to 71.871°; −6 ≤ h ≤ 6, −16 ≤ k ≤ 17, −8 ≤ l ≤ 8; 8309 reflections collected; 2124 independent reflections [R(int) = 0.0389]; completeness to θ = 71.871°: 97.8 %
Single-crystal XRD, absorption correction and transmission	Multi-scan; maximum and minimum transmission 1.00000 and 0.90809
Single-crystal XRD, refinement	Full-matrix least-squares on F²; data / restraints / parameters: 2124 / 1 / 155; goodness-of-fit on F²: 1.025
Single-crystal XRD, R indices	[I > 2σ(I)] R1 = 0.0460, wR2 = 0.1255; all data R1 = 0.0495, wR2 = 0.1345
Single-crystal XRD, largest difference peak and hole	0.16 and −0.30 e Å⁻³
Single-crystal XRD molecular-structure image	Image data were not transcribed
¹H and ¹³C NMR spectra	Image data were not transcribed

5
TLC Rf (10:1 petroleum ether : EtOAc, KMnO₄)	0.37
¹H NMR (400 MHz, CDCl₃)	δ 5.76–5.54 (m, 2H), 5.04–4.82 (m, 1H), 3.78 (s, 3H), 2.65 (s, 4H), 2.44–2.28 (m, 1H), 2.26–2.04 (m, 3H), 2.04–1.85 (m, 2H), 1.81 (s, 11H), 1.73–1.58 (m, 3H)
¹³C NMR (101 MHz, CDCl₃)	δ 161.83, 160.74, 143.40, 141.53, 129.83, 129.60, 76.45, 51.76, 33.61, 33.37, 27.13, 26.98, 25.54, 24.79, 22.29
HR-ESI-MS	C₁₅H₂₀NaO₄ [M+Na]⁺, Calculated: 287.1254; Found: 287.1254
¹H and ¹³C NMR spectra	Image data were not transcribed

6
TLC Rf (10:1 petroleum ether : EtOAc, KMnO₄)	0.23
¹H NMR (400 MHz, CDCl₃)	δ 5.75–5.57 (m, 2H), 4.99–4.88 (m, 1H), 3.79 (s, 3H), 2.64–2.54 (m, 2H), 2.34 (m, 1H), 2.24–2.03 (m, 3H), 1.92 (m, 44H), 1.84–1.51 (m, 4H)
¹³C NMR (101 MHz, CDCl₃)	δ 165.20, 165.18, 163.97, 163.93, 129.94, 129.85, 129.46, 129.39, 77.92, 77.86, 77.35, 77.03, 76.71, 64.67, 64.63, 64.30, 52.69, 33.59, 33.51, 33.47, 33.44, 27.92, 25.63, 25.61, 25.56, 25.51, 24.74, 22.19, 22.14
HR-ESI-MS	C₁₂H₂₄NaO₅ [M+Na]⁺, Calculated: 298.1649; Found: 298.1650
¹H and ¹³C NMR spectra	Image data were not transcribed

trans-7
TLC Rf (4:1 petroleum ether : EtOAc, KMnO₄)	0.22
¹H NMR (400 MHz, CDCl₃)	δ 5.58–5.20 (m, 2H), 4.73–4.26 (m, 4H), 4.21–4.04 (m, 1H), 3.75 (s, 3H), 3.71 (s, 3H), 3.60 (d, J = 5.6 Hz, 1H), 2.58–1.91 (m, 8H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.77, 168.87, 168.30, 128.11, 127.04, 88.59, 86.14, 68.61, 66.91, 54.63, 53.63, 52.99, 52.82, 34.72, 29.39, 29.13, 28.97
HR-ESI-MS	C₁₈H₂₂NaO₉ [M+Na]⁺, Calculated: 405.1156; Found: 405.1157
¹H and ¹³C NMR spectra	Image data were not transcribed

endo-7
TLC Rf (4:1 petroleum ether : EtOAc, KMnO₄)	0.35
¹H NMR (400 MHz, CDCl₃)	δ 5.49–5.36 (m, 2H), 4.39 (m, 4H), 3.73 (s, 1H), 3.70 (s, 3H), 2.55 (m, 2H), 2.48–2.18 (m, 6H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.51, 168.87, 128.24, 87.59, 67.36, 52.25, 50.70, 29.19, 29.03
HR-ESI-MS	C₁₈H₂₂NaO₉ [M+Na]⁺, Calculated: 405.1156; Found: 405.1157
¹H and ¹³C NMR spectra	Image data were not transcribed

exo-7
TLC Rf (4:1 petroleum ether : EtOAc, KMnO₄)	0.06
¹H NMR (400 MHz, CDCl₃)	δ 5.42 (td, J = 5.0, 2.4 Hz, 2H), 4.49 (dt, J = 10.6, 6.7 Hz, 2H), 4.28 (dt, J = 10.6, 6.8 Hz, 2H), 3.63 (s, 6H), 3.56 (s, 2H), 2.70 (s, 2H), 2.54 (s, 2H), 2.18–2.06 (m, 4H)
¹³C NMR (101 MHz, CDCl₃)	δ 169.57, 169.34, 127.23, 85.99, 68.37, 55.62, 52.39, 34.17, 28.95
HR-ESI-MS	C₁₈H₂₂NaO₉ [M+Na]⁺, Calculated: 405.1156; Found: 405.1157
Single-crystal XRD, empirical formula	C₁₈H₂₂O₉
Single-crystal XRD, formula mass	382.35 g mol⁻¹
Single-crystal XRD (180 K, λ = 1.54184 Å), crystal system and space group	monoclinic; P2₁/c
Single-crystal XRD, unit cell	a = 19.77940(8) Å, α = 90°; b = 9.10624(4) Å, β = 90.5949(4)°; c = 19.74485(5) Å, γ = 90°; V = 3556.17(3) Å³; Z = 8
Single-crystal XRD, calculated density	1.428 Mg m⁻³
Single-crystal XRD, absorption coefficient and F(000)	0.983 mm⁻¹; 1616
Single-crystal XRD, crystal size	0.3 × 0.25 × 0.2 mm³
Single-crystal XRD, data collection	θ = 2.234 to 72.454°; −24 ≤ h ≤ 24, −11 ≤ k ≤ 11, −23 ≤ l ≤ 24; 74253 reflections collected; 6849 independent reflections [R(int) = 0.0383]; completeness to θ = 72.454°: 97.1 %
Single-crystal XRD, absorption correction and transmission	Multi-scan; maximum and minimum transmission 1.00000 and 0.27747
Single-crystal XRD, refinement	Full-matrix least-squares on F²; data / restraints / parameters: 6849 / 0 / 512; goodness-of-fit on F²: 1.018
Single-crystal XRD, R indices	[I > 2σ(I)] R1 = 0.0341, wR2 = 0.0824; all data R1 = 0.0364, wR2 = 0.0838
Single-crystal XRD, largest difference peak and hole	0.28 and −0.19 e Å⁻³
Single-crystal XRD molecular-structure image	Image data were not transcribed
¹H and ¹³C NMR spectra	Image data were not transcribed

8
TLC Rf (10:1 petroleum ether : EtOAc, CAM)	0.54
¹H NMR (400 MHz, CDCl₃)	δ = 5.78 (ddt, J = 17.1, 10.3, 6.7 Hz, 2H), 5.16–5.03 (m, 4H), 4.15 (t, J = 6.7 Hz, 4H), 2.62 (s, 4H), 2.39 (qt, J = 6.8, 1.4 Hz, 4H)
¹³C NMR (100 MHz, CDCl₃)	δ = 172.38, 134.04, 117.42, 63.91, 33.15, 29.27
HR-ESI-MS	C₁₂H₁₈O₄Na [M+Na]⁺, Calculated: 249.1097; Found: 249.1098
¹H and ¹³C NMR spectra	Image data were not transcribed

9
TLC Rf (10:1 petroleum ether : EtOAc, KMnO₄)	0.21
¹H NMR (400 MHz, CDCl₃)	δ = 5.55–5.44 (m, 1H), 5.36–5.25 (m, 1H), 4.29–4.19 (m, 4H), 2.60 (d, J = 3.0 Hz, 4H), 2.44–2.28 (m, 4H)
¹³C NMR (100 MHz, CDCl₃)	δ = 171.96, 171.65, 129.50, 128.83, 63.36, 62.03, 33.40, 30.54, 30.35, 27.10
HR-ESI-MS	C₁₀H₁₅O₄ [M+H]⁺, Calculated: 199.0965; Found: 199.0966
¹H and ¹³C NMR spectra	Image data were not transcribed

10
TLC Rf (10:1 petroleum ether : EtOAc, CAM)	0.18
¹H NMR (400 MHz, CDCl₃)	δ 3.81 (s, 6H), 2.69 – 2.54 (m, 2H), 2.01 – 1.87 (m, 2H)
¹³C NMR (101 MHz, CDCl₃)	δ 164.91, 64.56, 52.87, 25.68
HR-ESI-MS	C₈H₁₀KO₅ [M+K]⁺, Calculated: 225.0160; Found: 225.0164
¹H and ¹³C NMR spectra	Image data were not transcribed

11
TLC Rf (1:2 petroleum ether : EtOAc, I₂)	0.30
¹H NMR (400 MHz, CDCl₃)	δ 3.76 (s, 12H), 2.91 – 2.84 (m, 4H), 2.20 – 2.13 (m, 4H)
¹³C NMR (151 MHz, CDCl₃)	δ 168.00, 89.87, 52.92, 31.33
HR-ESI-MS	C₁₆H₂₀KO₁₀ [M+K]⁺, Calculated: 411.0688; Found: 411.0690
¹H and ¹³C NMR spectra	Image data were not transcribed

P1
GPC trace (THF, 25 °C, refractive-index response)	Image data were not transcribed
¹H NMR spectrum (CDCl₃, 298 K, 400 MHz)	The ratio of incorporated comonomers was determined by relative peak integrations; image data were not transcribed

P2
¹H NMR comparison (CDCl₃, 298 K, 400 MHz)	P1 before and after sonication (P2), and model compound 10; P1: 142 kDa, m : n = 2.3, Đ = 1.7; no changes in the olefin region; a new set of proton peaks equivalent to ~20 % oBCP conversion was observed and assigned to oBCP-dimer; the structural assignment was corroborated by comparison with the independently synthesized dimethyl ester-substituted dimer model compound; image data were not transcribed
¹H–¹H COSY, ¹H–¹³C HSQC and HMBC (CDCl₃, 298 K, 600 MHz)	The product exhibited a characteristic 90-ppm quaternary carbon; image data were not transcribed
Experimental ¹³C NMR chemical-shift comparison	Image data were not transcribed

P1 sonication concentration series
¹H NMR after sonication with different diethyl fumarate concentrations	Image data were not transcribed
Mark–Houwink exponent α (1 mg mL⁻¹)	0.71 before sonication; ~0.3 after sonication-induced ring opening; the decrease in α correlated linearly with dimer formation quantified by ¹H NMR
GPC (Mₙ = 260 kDa, 0.5 mg mL⁻¹)	Molecular weight decreased monotonically from the outset during sonication; image data were not transcribed
GPC (Mₙ = 260 kDa, 10 mg mL⁻¹)	A bimodal distribution emerged in the initial stage, followed by a global molecular-weight decrease and eventual merging into a single peak; image data were not transcribed
GPC high-molecular-weight shoulder fraction during sonication	Obtained by peak deconvolution of the corresponding GPC traces; image data were not transcribed

P4
GPC trace (THF, 25 °C, refractive-index response)	Image data were not transcribed
¹H NMR spectrum (CDCl₃, 298 K, 400 MHz)	The ratio of incorporated comonomers was determined by relative peak integrations; image data were not transcribed

P8
GPC trace (THF, 25 °C, refractive-index response)	Image data were not transcribed
¹H NMR spectrum (CDCl₃, 298 K, 400 MHz)	The ratio of incorporated comonomers was determined by relative peak integrations; image data were not transcribed
¹H NMR after sonication with CT	[CT]₀ = 0.5 M, supersaturated; 223 kDa; m : n = 2.2; Đ = 2.0; low-level CT incorporation was observed; image data were not transcribed

P5
¹H NMR spectrum (CDCl₃, 298 K, 400 MHz)	P1 after sonication; [dimethyl maleate]₀ = 2.0 M; 141 kDa; m : n = 3.7; Đ = 2.3; the adduct was a mixture of possible diastereomers; image data were not transcribed
¹H–¹³C HSQC spectrum (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed
Experimental cis : trans product distribution	~1.6

P6
¹H NMR spectrum (CDCl₃, 298 K, 400 MHz)	P1 after sonication; [dimethyl fumarate]₀ = 0.5 M, supersaturated; 142 kDa; m : n = 2.3; Đ = 1.7; the adduct was a mixture of possible diastereomers; image data were not transcribed
¹H–¹³C HSQC spectrum (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed
Stereochemical assignment by ¹H NMR comparison with reference compounds	The chemically distinctive ester α-proton peaks indicated that the two ester groups were in trans configuration

P7
¹H NMR and GPC with UV–Vis detection	P1 after sonication; [CT]₀ = 0.5 M, supersaturated; 227 kDa; m : n = 3.9; Đ = 2.1; substantial chromophore incorporation (~20 %) was observed; image data were not transcribed
DOSY spectrum	The overestimated diffusion coefficient was attributed to accelerated NMR signal decay due to the presence of paramagnetic radicals on the polymer; image data were not transcribed

P9: Methyl acrylate
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 141 k, m : n = 3.7, Đ = 2.3; image data were not transcribed

P10: 2-Hydroxyethyl acrylate
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 214 k, m : n = 2.9, Đ = 2.8; image data were not transcribed
¹H NMR before and after sonication with 2.0 M 2-hydroxyethyl acrylate (CDCl₃, 298 K, 400 MHz)	P1: 233 k, m : n = 3.4, Đ = 2.3; image data were not transcribed
¹H–¹H COSY and ¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Correlation peaks were associated with the endo and exo products; image data were not transcribed
Static water-contact angle	63°, compared with 94° for P1

P11: N,N-dimethylacrylamide
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 141 k, m : n = 3.7, Đ = 2.3; image data were not transcribed
¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed

P12: Acrylonitrile
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 146 k, m : n = 3.3, Đ = 2.0; image data were not transcribed
¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed

P13: Pinacol vinylboronate
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 146 k, m : n = 3.3, Đ = 2.0; image data were not transcribed
¹H–¹H COSY and ¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed

P14: Phenyl vinyl sulfone
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 146 k, m : n = 3.3, Đ = 2.0; image data were not transcribed
¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed

P15: Styrene
¹H NMR before and after sonication (CD₂Cl₂, 298 K, 400 MHz)	P1: 214 k, m : n = 2.9, Đ = 2.8; image data were not transcribed
¹H–¹³C HSQC (CD₂Cl₂, 298 K, 600 MHz)	Image data were not transcribed

P16: 4-Chlorostyrene
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 146 k, m : n = 3.3, Đ = 2.0; image data were not transcribed
¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed

P17: 4-Methoxystyrene
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 146 k, m : n = 3.3, Đ = 2.0; image data were not transcribed

P18: 2-Vinylpyridine
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 142 k, m : n = 3.7, Đ = 2.0; image data were not transcribed

P19: Methyl methacrylate
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 146 k, m : n = 3.3, Đ = 2.0; sonication also led to polymerization of methyl methacrylate as a side product; image data were not transcribed

P20: Methyl cinnamate
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 141 k, m : n = 3.7, Đ = 2.3; image data were not transcribed
¹H–¹H COSY and ¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Correlation peaks were associated with the endo and exo products; image data were not transcribed

P21: Coumarin
¹H NMR before and after sonication (CD₂Cl₂, 298 K, 400 MHz)	P1: 214 k, m : n = 2.9, Đ = 2.8; image data were not transcribed
¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed

P22: Maleic anhydride
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 142 k, m : n = 3.7, Đ = 2.0; image data were not transcribed

P23: N-ethylmaleimide
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 142 k, m : n = 3.7, Đ = 2.0; image data were not transcribed
¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed

P24: 5-Norbornene-2-ylacetate
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 142 k, m : n = 3.7, Đ = 2.0; image data were not transcribed
¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Correlation peaks were associated with the endo and exo products; image data were not transcribed

P25: Dimethyl acetylenedicarboxylate
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 141 k, m : n = 3.7, Đ = 2.3; image data were not transcribed

P26: Methyl propiolate
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 141 k, m : n = 3.7, Đ = 2.3; image data were not transcribed

P27: Thiobenzoylmercaptoacetic acid
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 142 k, m : n = 3.7, Đ = 2.0; image data were not transcribed
¹H–¹³C HSQC (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed

P28: Diethyl azodicarboxylate
¹H NMR before and after sonication (CDCl₃, 298 K, 400 MHz)	P1: 142 k, m : n = 3.7, Đ = 2.0; image data were not transcribed
¹H–¹H COSY (CDCl₃, 298 K, 600 MHz)	Image data were not transcribed

P29: MA-violet13
Appearance after sonication	The initially colorless polymer solution became purple-red
GPC with UV–Vis detection	Strong absorption at 508 nm; image data were not transcribed
¹H NMR comparison (CDCl₃, 298 K, 400 MHz)	P1; P1 (233 k, m : n = 3.4, Đ = 2.3) sonicated with 0.05 M MA-violet13 (P29); and MA-violet13; image data were not transcribed

P30
¹H NMR comparison with P1 and P31 (CDCl₃, 298 K, 400 MHz)	P1: 233 k, m : n = 3.4, Đ = 2.3; image data were not transcribed
GPC	Mₙ = 37 kDa, Đ = 1.75; image data were not transcribed

P31
¹H NMR comparison with P1 and P30 (CDCl₃, 298 K, 400 MHz)	P1: 233 k, m : n = 3.4, Đ = 2.3; characteristic poly(methyl acrylate) side-chain signals appeared; image data were not transcribed
GPC molecular weight	53 kDa, increased from 37 kDa for P30; image data were not transcribed