Av neo 400

¹H NMR and HSQC spectra were recorded on a Bruker AVNEO400 instrument (Bruker, Rheinstetten, Germany). CD3OD was used as solvent for the total and polar extracts, and CDCl3 was used for the scCO₂ extract.

All reactions were carried out under an argon atmosphere. Commercial-grade reagents and solvents were used without further purification, except for THF, which was dried by distillation over Na/benzophenone before use. NMR spectra were recorded on Bruker AV Neo 400 (Bruker, Billerica, MA, USA) spectrometer. Chemical shifts of ¹H and ¹³C are reported relative to the residual proton resonance in the deuterated solvents. Chemical shifts (δ) are provided in ppm. HRMS measurements were performed on a Finnigan MAT 95 (Thermo Fisher Scientific, Waltham, MA, USA) or Waters Synapt HDMS (Waters Corporation, Milford, MA, USA) mass spectrometer. Melting points are uncorrected. 4-(N,N-bis(6-iodohexyl)amino)benzaldehyde [45 (link)], 4-(N,N-dimethylamino)benzaldehyde [67 (link)], 2,6-bis[(diethoxyphosphoryl)methyl]dithieno[3,2-b:2′,3′-d]thiophene-4,4-dioxide [48 (link)] and 4,4′-bis(4′-{N,N-bis[6”-(trimethylammonium)hexyl]amino}styryl)stilbene (DSSN-NMe₃⁺) [68 (link)] were prepared according to procedures outlined in the literature. NMR spectra of DTTDO-NMe₃⁺ and DTTDO derivative 2 are available in Supplementary Materials.

¹H NMR, ¹³C NMR (DEPTQ), ¹⁹F-NMR, and 2D NMR spectra were recorded
in CDCl₃ or DMSO-d₆ (Merck
KGaA, Darmstadt, Germany) on Bruker AV NEO 400, AV NEO 500 WB, AV
III 600 or AV III HD 700 spectrometers (Bruker, Mannheim, Germany).
Spectra evaluation was performed using MestReNova 14.2 software (Mestrelab
Research S.L., Santiago de Compostela, Spain).
Full-scan high-resolution
mass spectra (m/z 50–1600)
of the compounds dissolved in MeCN/MeOH and 1% H₂O were
obtained by direct infusion measurements on a maXis ESI-Qq-TOF mass
spectrometer (Bruker, Mannheim, Germany). The sum formulas of the
detected ions were determined using Compass DataAnalysis 4.0 (Bruker,
Mannheim, Germany) based on the mass accuracy (Δm/z ≤ 5 ppm) and isotopic pattern matching
(SmartFormula algorithm).
Compound characterization data is
provided in the Supporting Information
(Figures S10–S19).