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. 2007 May 29;104(24):9937–9942. doi: 10.1073/pnas.0703748104

Scheme 1.

Scheme 1.

Synthesis of the azo-functionalized rod 1 comprising a terminal sulfur group. (Reaction a) Step 1: NH4Cl, Zn, MeOCH2CH2OH, and H2O at 35°C. Step 2: FeCl3, MeOCH2CH2OH, H2O, and EtOH at −5°C, 63%. (Reaction b) NaSMe and DMI at 150°C, 60%. (Reaction c) mCPBA and CH2Cl2 at 0°C, 89%. (Reaction d) (Ph)2C = NH, [Pd2(dba)3]·CHCl3, KOtBu, BINAP, and CH3C6H5 at 80°C, 77%. (Reaction e) NH2OH·HCl, NaOAc, and MeOH at room temperature, 95%. (Reaction f) AcOH and CH2Cl2 at 65°C, 83%. (Reaction g) Step 1: (CF3CO)2O and CH3C6H5 at 40°C. Step 2: Et3N, CH3C6H5 and EtOH, at room temperature, 27%. Detailed information on the synthesis and characterization are given in the SI Text.