S1 Electronic Supplementary Information for Doubly N-confused isophlorin: Synthesis, structure and copper coordination Jiaying Yan, Makoto Takakusaki, Yufeng Yang, Shigeki Mori, Bao Zhang, Yaqing Feng, * Masatoshi Ishida and Hiroyuki Furuta * Table of Contents Experimental general ---------------------------------------------------------------------------------------S2 Preparation of 2, 3, 4-Cu ------------------------------------------------------------------------------ S2–S3 Fig. S1: HPLC charts for 2, 3, 4-Cu-------------------------------------------------------------------------S4 Fig. S2–S10: 1 H, 19 F, 13 C-NMR spectra of 2, 3, 4-Cu ---------------------------------------------- S5–S9 Fig. S11: 1 H NMR spectral changes of 2 upon addition of D 2 O ----------------------------------------S9 Fig. S12–S13: 1 H- 1 H COSY spectra of 2, 4-Cu in CDCl 3 ---------------------------------------------S10 Fig. S14: UV/vis absorption spectrum of 4-Cu in CH 2 Cl 2 ---------------------------------------------S11 Fig. S15: CV and DPV of 2, 3, 4-Cu in CH 2 Cl 2 ---------------------------------------------------------S11 X-ray details: ------------------------------------------------------------------------------------------------S12 Table S1: Crystal data and structure analysis results for 2, 3, 4-Cu ----------------------------------S13 Fig. S16–S17: X-ray crystal structures of 2, 3 -----------------------------------------------------------S14 Fig. S18–S19: Selected bond lengths (Å) and C-N-C angles (deg) of 2, 3, 4-Cu ------------------S15 Calculation details: ----------------------------------------------------------------------------------------S16 Fig. S20: Optimized structures of 2 and 3 obtained by DFT calculations ---------------------------S17 Table S2: HOMA values calculated for 2, 3, 4-Cu -----------------------------------------------------S17 Fig. S21: NICS values (ppm) of 2, 3, 4-Cu -----------------------------------------------------------S18 Fig. S22: MO diagrams of 2, 3, 4-Cu ---------------------------------------------------------------------S18 Fig. S23: TD-DFT calculations for 2, 3, 4-Cu -----------------------------------------------------------S19 Cartesian coordinates for the optimized structures for 2, 3, 4-Cu -------------------------S20–S28 Electronic Supplementary Material (ESI) for ChemComm. This journal is © The Royal Society of Chemistry 2014