Mercury plus 300

ADP@SWNT was synthesized by ultrasonic approaches. Briefly, 5 mg of SWNTs were placed in 10 mL of distilled water and sonicated using an ultrasonic probe (Sigma Ultrasonic Processor, GEX‐600). This process proceeded at 30 W for 20 min, during which each pulse lasted for 2 s followed by 2 s of rest. Sonication was repeated three times with a 10‐min suspension each time. Next, 10 mg of ADP was added to the above solution and sonicated for 30 min at 130 W, 50 Hz, and 50%. Similarly, the pulse width was 2 s (pulse period of 4 s), and this step was repeated three times with a 10‐min suspension each time. The resulting suspension was stirred for 12 h and centrifuged at 3000 r/s for 10 min, followed by filtration and lyophilization procedures. Finally, the inclusion complex, a PLLD‐G3‐based functionalized amylose derivative loaded with SWNTs, was obtained, with a yield of 47%. Infrared spectra were measured via the KBr squash method using an FTIR spectrophotometer (Nicolet 670, Thermo Nicolet Corporation, Wisconsin, USA). ¹H NMR analyses (Mercury‐Plus 300 Varian, USA) for the PLLD‐G3, Amy‐N3, ADP and ADP@SWNT dispersions were used to confirm the formation of ADP@SWNT. Circular dichroism (CD) spectra measurements of the ADP, SWNTs, PLLD‐G3, ADP + SWNT and ADP@SWNT dispersions (1 mg/mL) were carried out using a J‐810 circular dichroism spectropolarimeter (Jasco, Easton, MD, USA).

Proton and carbon nuclear magnetic resonance (¹H-NMR, ¹³C-NMR) experiments were performed on Varian Unity-500, Unity Plus-300, and Mercury Plus-300 instruments (Varian, Palo Alto, CA, USA). Deuterated chloroform (CDCl₃) and deuterated methanol (CD₃OD) were used as solvents. Total correlation spectroscopy (TOCSY) experiments were performed on selected compounds for further characterization insight.

NMR spectra were recorded at room temperature using a Bruker Avance 300 (300 MHz for ¹H, 75 MHz for ¹³C), a Bruker Avance 400 (400 MHz for ¹H, 101 MHz for ¹³C), an Agilent 400-MR DDR2 (400 MHz for ¹H and 101 MHz for ¹³C), or a Varian Mercury Plus 300 (300 MHz for ¹H, 75 MHz for ¹³C) with internal solvent signal as reference. All chemical shifts are reported in δ-scale as parts per million (multiplicity, coupling constant J, number of protons) relative to the solvent residual peaks as the internal standard (IS). NMR spectra are available in Supplementary Figs. 13–22.

The data of the chemical structure of the isolated compound were determined by proton and carbon (¹H and ¹³C) distribution, ¹H-¹³C heteronuclear single quantum correlation (HSQC) and ¹H-¹³C heteronuclear bond multiple correlation (HMBC) [32 (link)]. The nuclear magnetic resonance (NMR) spectra were recorded on a Varian Mercury Plus 300 (Varian Inc., Palo Alto, CA, USA) spectrometer with tetramethylsilane (TSM) as an internal standard. The hydrogen (¹H) NMR spectra were measured at 600 MHz, while the carbon (¹³C) NMR spectra were measured at 100 MHz. The NMR was performed at a constant temperature of 27 °C using the software supplied by the manufacturer. The solvent used for dissolution was deuterated chloroform (CDCl₃). The chemical shifts (δ) were expressed in parts per million (PPM), and the coupling constant (J) was expressed in Hertz (Hz).

All reactions were performed under argon atmosphere. NMR spectra were measured on Varian MercuryPlus 300 (¹H, 300.13 MHz; ¹³C, 75.46 MHz), Agilent 400 MR DD2 (¹H, 400.13 MHz; ¹³C, 100.61 MHz) or Bruker Avance III 500 (³¹P, 202.45 MHz) spectrometer at 298 K. Chemical shifts of 31P NMR spectra are referenced to the signal of 85% H₃PO₄ that was assigned the chemical shift of 0. Mass spectra were measured on ZAB-SEQ (VG Analytical). The dry and degassed THF was prepared by PureSolv MD7. Silica gel (Merck, Silica Gel 60, 40–63 μm or Merck Silica Gel 60, 63–200 μm) was used for column chromatography. A phosphate 2a was prepared according to a published procedure.^{30 (link)}n-BuLi (2.5 M solution in hexane), and other compounds were purchased from Sigma-Aldrich, FLuorochem and Acros Organics. Concentration of BuLi was determined by titration using menthol and 1,10-phenanthroline before use.