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. 2020 Oct 28;5(44):28606–28614. doi: 10.1021/acsomega.0c03565

Scheme 2. Synthesis and Structures of Triptycen-Based Luminescent Molecules.

Scheme 2

Reagents and conditions: (i) with modified procedures in ref (16): (a) vinylene carbonate, hydroquinone (5%), 190 °C, 3 d; (b) KOH, H2O, reflux; (c) trifluoroacetic anhydride, N-ethyldiisopropylamine, DCM/DMSO, −60 °C to r.t., overnight, and treatment with HCl; (d) o-phenylenediamine (1.0 equiv), pyridine, 65 °C. (ii) Carbazole (2.0 equiv), CuI (5%), o-C6H4Cl2, 180 °C. (iii) Phenothiazine (2.2 equiv), Pd2(dba)3 (5%), t-Bu3P, t-BuONa, toluene, reflux. (iv) Carbazole (1.0 equiv), CuI (5%), o-C6H4Cl2, 180 °C. (v) Phenothiazine (1.0 equiv), CuI (5%), o-C6H4Cl2, 180 °C. (vi) For Cz–BMes and Pz–BMes: Mes2BC6H4B(OH)2, Pd(PPh3)4 (5%), K2CO3, toluene/H2O, reflux. For Cz–Npa, Pz–Npa, Cz–NpaBr, and Pz–NpaBr: (a) benzophenonimine, Pd2(dba)3 (5%), BINAP, t-BuONa, 107 °C; (b) treatment with HCl and THF; (c) (bromo)naphthalic anhydride, HOAc, reflux, 5 h.