Potassium phthalimide

Barium oxide (BaO, 90%, ACROS), calcium hydride (CaH₂, Sigma-Aldrich), triethylamine (TEA, Sigma-Aldrich), potassium phthalimide (Sigma-Aldrich), hydrazine monohydrate (N₂H₂, 64 to 66% N₂H₄, Sigma-Aldrich), sodium trifluoroacetate (NaTFA, 98%, Sigma-Aldrich), 2,5-dihydroxybenzoic acid (DHB, 98%, Sigma-Aldrich) were used as purchased. Prior to use, 2-ethyl-2-oxazoline (EtOx, Sigma-Aldrich) and 2-methyl-2-oxazoline (MeOx, Sigma-Aldrich) were stirred over BaO overnight, distilled and stored under argon atmosphere. Methyl p-tosylate (MeTos, Sigma-Aldrich) was pre-dried over CaH₂, distilled under reduced pressure and stored under argon atmosphere. Acetonitrile was obtained from a solvent purification system (SPS; Pure solv EN, InnovativeTechnology). HPLC and MS grade acetonitrile and water for HPLC measurements were obtained from VWR. All other chemicals and solvents were received from common commercial sources and used without further purification unless otherwise stated.

Thiophene (≥99%), N-bromosuccinimide (NBS) (99%), N,N-dimethylformamide (DMF) (≥99%), dichloromethane (DCM) (≥99.5%), 2-(tributylstannyl)Thiophene (97%), bis(triphenylphosphine)palladium(II) dichloride [PdCl₂(PPh₃)₂] (98%), N-thionylaniline (PhNSO) (98%), chlorotrimethylsilane [(CH₃)₃SiCl] (≥98%), pyridine (99.8%), xylene (≥99%), triphenylphosphine (Ph₃P) (99%), 3,7-dimethyl-1-octanol (≥98%), potassium phthalimide(98%), hydrazine hydrate (50–60%), octylamine (99%), palladium(II) acetate [Pd(OAc)₂] (98%), anhydrous acetic anhydride (≥99%), acetic acid (≥99%) and tris(o-tolyl)phosphine [P(o-tol)₃] (97%) were purchased from Sigma-Aldrich (Gillingham, UK). Anhydrous tin(II) chloride (98%) and dimethyl acetylenedicarboxylate (98%) were purchased from Alfa Aesar (Heysham, UK). All of the starting materials and reagents obtained from Sigma-Aldrich and Alfa Aesar were utilized without further purification. The majority of the reactions were carried out under argon atmosphere. Anhydrous solvents used for the reactions obtained from Grubbs solvent purification system within the Sheffield University/Chemistry department. 9,10-Bis(4-(dodecyloxy)phenyl)-2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) anthracene (M3) [21 (link)] was prepared according to literature procedure.