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1 Supporting Information Molecular Cage Impregnated Palladium Nanoparticles: Efficient, Additive-Free Heterogeneous Catalysts for Cyanation of Aryl Halides. Bijnaneswar Mondal, Koushik Acharyya, Prodip Howlader and Partha Sarathi Mukherjee* Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore , India. Fax: ; Tel; These authors contributed equally. Figure S1: 1 H NMR spectrum of aldehyde C recorded in CDCl 3. S1

2 Figure S2: 13 C NMR spectrum of aldehyde C recorded in CDCl 3. Figure S3: ESI-HRMS spectrum of aldehyde C recorded in CH 3 CN. S2

3 Figure S4: FTIR spectrum of aldehyde C. Figure S5: ORTEP diagram of aldehyde C. S3

4 Figure S6: Unit cell packing diagram of aldehyde C. Hydrogen atoms are omitted for clarity. Table S1: Crystallographic data and refinement parameters for aldehyde C. Empirical formula C 39 H 27 NO 3 Fw T (K) 100 crystal system Triclinic space group P a/å (10) b/å (14) c/å (16) α/deg (3) β/deg (3) γ/deg (3) V/Å (3) Z 2 ρcalcd (g cm -3 ) μ(mo K) (mm -1 ) λ/å F (000) unique reflns 6471 GOF (F 2 ) a R b wr [a] R 1 = Σ F o F c / Σ F o. [b] wr 2 = [Σ{w(F 2 o F 2 c ) 2 }/Σ{w(F 2 o ) 2 }] 1/2 S4

5 Figure S7: 1 H NMR spectrum of the cage CC1 recorded in CDCl 3. Figure S8: 13 C NMR spectrum of the cage CC1 recorded in CDCl 3. S5

6 Figure S9: 1 H- 1 H COSY NMR spectrum of the cage CC1 recorded in CDCl 3 Figure S10: 1 H- 13 C HMQC NMR spectrum of the cage CC1 recorded in CDCl 3. S6

7 Figure S11: FTIR spectrum of CC1. Figure S12: ESI-HRMS spectrum of CC1 recorded in CHCl 3 -CH 3 CN (1:1, v/v). S7

8 Figure S13: 1 H NMR spectrum of the cage CC1 r recorded in CDCl 3. Figure S14: 13 C NMR spectrum of the cage CC1 r recorded in CDCl 3. S8

9 Figure S15: 1 H- 1 H COSY NMR spectrum of the cage CC1 r recorded in CDCl 3. Figure S16: 1 H- 13 C HMQC NMR spectrum of the cage CC1 r recorded in CDCl 3. S9

10 Figure S17: FTIR spectrum of CC1 r. Figure S18: Molecular dimensions of CC1 r based on DFT calculation. S10

11 Scheme S1: Synthesis of CC2 r from tris(4-formylphenyl)amine (E) with (S, S)-1, 2- diaminocyclohexane (D) by employing dynamic imine chemistry followed by imine bond reduction. S11

12 Figure S19: 1 H NMR spectrum of CC2 recorded in CDCl 3. Figure S20: ESI-HRMS spectrum of CC2 recorded in CHCl 3 -MeOH. S12

13 Figure S21: 1 H NMR spectrum of CC2 r recorded in CDCl 3. Figure S22: ESI-HRMS spectrum of CC2 r recorded in CHCl 3 -MeOH. S13

14 Figure S23: Visual color changes during cage supported nanoparticle synthesis. (a) r and (b) r. Figure S24: PXRD pattern of r and CC1 r. S14

15 Figure S25: (a) SEM, (b) TEM, (c) particle size distribution and (d) XPS spectrum of r. Figure S26: PXRD pattern of r and CC2 r. S15

16 Figure S27: TEM image of as synthesized PDNPs in absence of cage compounds. Figure S28: TEM image and particle size distribution of (a) r and (b) r after 5 cycles. S16

17 Scheme S2: Schematic illustration of preparation of heterogeneous catalyst r. Figure S29: 1 H NMR spectrum of 4-formylbenzonitrile recorded in CDCl 3. S17

18 Figure S30: 13 C NMR spectrum of 4-formylbenzonitrile recorded in CDCl 3. Figure S31: 1 H NMR spectrum of 4-nitrolbenzonitrile recorded in CDCl 3 S18

19 Figure S32: 13 C NMR spectrum of 4-nitrolbenzonitrile recorded in CDCl 3. Figure S33: 1 H NMR spectrum of 4-cyanoacetophenon recorded in CDCl 3. S19

20 Figure S34: 13 C NMR spectrum of 4-cyanoacetophenon recorded in CDCl 3. Figure S35: 1 H NMR spectrum of 4-cyanobenzoic acid recorded in CD 3 OD. S20

21 Figure S36: 13 C NMR spectrum of 4-cyanobenzoic acid recorded in CD 3 OD. Figure S37: 1 H NMR spectrum of 5-cyanopyrimidine recorded in CDCl 3. S21

22 Figure S38: 13 C NMR spectrum of 5-cyanopyrimidine recorded in CDCl 3. Figure S39: 1 H NMR spectrum of 1,4-dicyanobenzene recorded in CDCl 3. S22

23 Figure S40: 13 C NMR spectrum of 1,4-dicyanobenzene recorded in CDCl 3. Figure S41: 1 H NMR spectrum of benzonitrile recorded in CDCl 3. S23

24 Figure S42: 13 C NMR spectrum of benzonitrile recorded in CDCl 3. Figure S43: 1 H NMR spectrum of 4-pyridinecarbonitrile recorded in CDCl 3. S24

25 Figure S44: 13 C NMR spectrum of 4-pyridinecarbonitrile recorded in CDCl 3. Figure S45: 1 H NMR spectrum of 3-pyridinecarbonitrile recorded in CDCl 3. S25

26 Figure S46: 13 C NMR spectrum of 3-pyridinecarbonitrile recorded in CDCl 3. Figure S47: 1 H NMR spectrum of 1,3,5-tricyanobenzene recorded in CDCl 3. S26

27 Figure S48: 1 H NMR spectrum of 1,3,5-tricyanobenzene recorded in DMSO-d 6. CC Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S27

28 S28

29 S29

30 S30

31 CC1 r Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S31

32 S32

33 S33

34 S34

35 CC2 r Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S35

36 S36

37 S37

38 S38

39 S39

40 S40

41 S41

42 S42

43 S43

44 S44

45 S45

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