N buli

The rare earth chlorides RECl₃ • 6 H₂O (RE: Y³⁺; Yb³⁺; purities > 99.9%) and oleic acid (OA, 90% purity) were purchased from Alfa Aesar (Havelhill, MA, USA), Tm³⁺ chloride (TmCl₃ • 6 H₂O, >99.9%), ammonium fluoride (NH₄F, 99%), cyclohexane (99.5%) and 3-(N-Morpholino)propanesulfonic acid (MOPS) were purchased from Sigma Aldrich (San Luis, AZ, USA). Ethanol (≥99.8%) and sodium hydroxide (NaOH, ≥99%) were purchased from Carl Roth (Karlsruhe, Germany), and Therminol^®66 was purchased from FRAGOL GmbH+Co. KG (Mülheim, Germany). Sodium oleate was synthesized by the authors using NaOH, Ethanol and OA. All chemical reagents were used as received without further purification.
For the synthesis of DBD-6, n-BuLi (1.6 M in hexane), decanal (95%), trimethylsilyldiazomethane (2 M in hexane), NaOH (98%), mEthanol (>99%) and tetrahydrofuran (>99.5%) were purchased from Acros organics (Morris, AL, USA), acetonitrile (>99.5%) and hydrochloric acid (HCl, 37%) from VWR (Randor, PA, USA), and glutaric acid anhydride was purchased from ABCR (Karlsruhe, Germany).

Reactions were carried out under dry nitrogen, using double manifold and glove-box methods. Solvents were distilled off sodium (toluene) or sodium–potassium amalgam (THF, hexane) immediately before use. 2,2,6,6-Tetramethylpiperidine (TMPH) was purchased from Alfa Aesar and stored over molecular sieves (4 Å). Other chemicals were used as received. nBuLi (1.6 M in hexanes) was purchased from Acros and used as received. For details of the syntheses of Ba(OCN)₂6,³² CuOCN 7 (ref. 32 ) and (TMPH₂)OCN 10 see the ESI.† The syntheses of reference materials TMPLi 9b and TMPCu 9c were based on the literature^{36 (link),43 (link)} and details are provided in the ESI.† IR spectra were collected on a Perkin Elmer Spectrum One FT IR spectrometer. The abbreviations used are: m = medium, s = strong. NMR data were collected on a Bruker Avance III HD 500 MHz Smart Probe FT NMR spectrometer (500.200 MHz for ¹H, 125.775 MHz for ¹³C, 194.397 for ⁷Li). Spectra were obtained at 25 °C using deuterated solvent stored over molecular sieves (3 Å). For ¹H and ¹³C, chemical shifts are internally referenced to deuterated solvent and calculated relative to TMS. For ⁷Li, an external reference was used (1 M LiCl in D₂O). Chemical shifts are expressed in δ ppm. The following abbreviations are used: br = broad, m = multiplet, s = singlet, sh = shoulder.