Coordination Polymers Containing Ferrocene Backbone. Synthesis, Structure and Electrochemistry

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Coordination Polymers Containing Ferrocene Backbone. Synthesis, Structure and Electrochemistry Vadapalli Chandrasekhar*, and Ramalingam Thirumoorthi Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India e-mail: vc@iitk.ac.in Tel: 91-512-2597259, Fax: 91-512-2590007/2597436. [ ] Prof. V. Chandrasekhar Department of Chemistry Indian Institute of Technology, Kanpur Kanpur 208016, India Fax: (+91)-512-2597436 E-mail: vc@iitk.ac.in

Alternate procedure for the synthesis of 3-6: A mixture of 2 (0.050 g, 0.050 mmol), 4-methylpyridine (0.005 g) /4,4 -bipyridine (0.008 g) or 4,4 - trimethylenebipyridine (0.010 g) or 4,4 -vinylenebipyridine (0.009 g) were heated in toluene (20 ml) under reflux for 2h. The reaction mixture was cooled and the solvent removed in vacuo to afford a yellow solid. This was washed with hexane (10 ml), Et 2 O (2 ml) dried and recrystallised to give pure samples of 3-6.

Figure S1. UV-visible spectra of 2-8.

Figure S2. ESI-MS of 2.

Figure S3. ESI-MS of 6. Inset picture shows the isotopic pattern of [(Ph 3 Sn) 2 LH(bpe)] +.

Figure S4. ESI-MS of 7.

Figure S5. ESI-MS of 8. Inset picture shows the isotopic pattern of [(n-bu 3 Sn) 4 (L)(LH)] +.

Figure S6. 2D polymeric structure of 8. Hydrogen atoms have been omitted.. Supramolecular structures of 2 and 5 Compound 2 shows an interesting supramolecular assembly in the solid-state due to two different types of π-stacking interactions. A C-H π interaction between the ferrocenyl C-H and the aromatic phenyl substituent on the tin (H22 π 2.5025(2) Å) leads to the formation of a 1D polymer. Further, two such 1D polymers are interconnected by C-H of the edge of aryl with face of other aryl groups leading to a 2D polymer (H42 π 3.4894 (42); H41 π 3.0791 (41); H38 π 2.8697 (41); H39 π 3.2544 (41) Å) (Figure S7). In compound 5 we have observed interaction between two 1D polymers through dichloromethane due to two different C-H Cl interactions (H10 Cl2 2.8622(26) and H37 Cl1 2.8528(20) Å) between the chlorine atoms of dichloromethane and the C-H of the aryl group and a ferrocenyl group (Figure S8).

Figure S7. 2D polymeric structure of 2. 2D polymers arises due to two different C-H π interaction between molecules.

Figures S8. C-H Cl interactions between two different 1D polymers of 5. Except H10 and H37 remaining all the hydrogen atoms are removed for the clarity.

Table S1. Selected bond lengths (Å) and angles ( ) for compounds 2-5 Sn(1)-O(1) Sn(2)-O(2) Sn(1)-O(4) Sn(2)-O(3) 2.093(3) 2.061(3) 2.552(3) 2.794(3) 2 C(19)-O(1) C(30)-O(2) C(30)-O(3) C(19)-O(4) 1.324(5) 1.314(5) 1.225(5) 1.233(5) O(1)-Sn(1)-O(4) O(1)-Sn(1)-C(13) O(1)-Sn(1)-C(1) C(13)-Sn(1)-C(1) C(1)-Sn(1)-O(4) C(7)-Sn(1)-O(4) C(31)-Sn(2)-C(43) O(2)-Sn(2)-C(37) Sn(1)-O(2) Sn(1)-N(1) 55.93(10) 104.50(13) 108.83(13) 125.68(16) 83.10(13) 155.31(14) 113.83(17) 113.53(14) 2.146(4) 2.485(4) 3 O(1)-Sn(1)-C(7) C(13)-Sn(1)-C(7) C(1)-Sn(1)-C(7) C(13)-Sn(1)-O(4) O(2)-Sn(2)-C(31) O(2)-Sn(2)-C(43) C(31)-Sn(2)-C(37) C(43)-Sn(2)-C(37) O(1)-C(25) O(2)-C(25) 99.66(14) 111.20(16) 104.04(16) 81.55(13) 105.02(14) 97.84 (14) 116.97(17) 108.08(16) 1.210(7) 1.301(6) C(19)-Sn(1)-C(7) C(19)-Sn(1)-O(2) C(7)-Sn(1)-O(2) C(19)-Sn(1)-C(13) C(7)-Sn(1)-C(13) Sn(1)-O(1) Sn(2)-O(3) Sn(1)-N(1) 126.4(2) 96.28(17) 97.86(16) 118.04(19) 113.52(19) 2.121(3) 2.121(3) 2.621(4) 4 O(2)-Sn(1)-C(13) C(19)-Sn(1)-N(1) C(7)-Sn(1)-N(1) O(2)-Sn(1)-N(1) C(13)-Sn(1)-N(1) Sn(2)-N(2) C(1)-O(1) C(1)-O(2) 89.54(17) 84.40(17) 83.97(16) 177.07(14) 87.64(17) 2.628(4) 1.314(6) 1.220(6) O(1)-Sn(1)-C(8) O(1)-Sn(1)-C(14) C(8)-Sn(1)-C(14) O(1)-Sn(1)-C(2) C(8)-Sn(1)-C(2) C(14)-Sn(1)-C(2) Sn(1)-O(1) Sn(2)-O(3) 98.82(16) 94.44(15) 130.65(19) 90.93(16) 112.99(18) 114.08(18) 2.135(4) 2.107(4) 5 C(42)-Sn(2)-O(3) C(42)-Sn(2)-C(30) O(3)-Sn(2)-C(30) C(42)-Sn(2)-C(36) O(3)-Sn(2)-C(36) C(30)-Sn(2)-C(36) C(32)-O(1) C(32)-O(2) 102.01(15) 130.11(18) 92.86(15) 113.34(18) 90.87(16) 113.74(19) 1.295(7) 1.237(7)

Sn(1)-N(2) Sn(2)-N(1) 2.598(4) 2.667(5) C(43)-O(3) C(43)-O(4) 1.313(7) 1.216(7) C(20)-Sn(1)-C(26) C(20)-Sn(1)-O(1) C(26)-Sn(1)-O(1) C(20)-Sn(1)-C(14) C(26)-Sn(1)-C(14) O(1)-Sn(1)-C(14) C(20)-Sn(1)-N(2) C(26)-Sn(1)-N(2) 129.5(2) 95.17(18) 97.37(17) 115.4(2) 113.5(2) 89.56(18) 84.54(18) 83.33(17) O(1)-Sn(1)-N(2) C(14)-Sn(1)-N(2) C(50)-Sn(2)-O(3) C(50)-Sn(2)-C(56) O(3)-Sn(2)-C(56) C(50)-Sn(2)-C(44) O(3)-Sn(2)-C(44) C(56)-Sn(2)-C(44) Table S2. Selected bond lengths (Å) and angles ( ) for compounds 6-8 179.26(14) 89.95(18) 97.19(17) 126.9(2) 96.47(19) 116.5(2) 89.89(19) 114.6(2) Sn(1)-O(1) Sn(1)-N(1) 2.127(3) 2.579(4) 6 O(1)-C(6) O(2)-C(6) 1.316(6) 1.214(6) C(13)-Sn(1)-O(1) C(13)-Sn(1)-C(7) O(1)-Sn(1)-C(7) C(13)-Sn(1)-C(19) O(1)-Sn(1)-C(19) C(7)-Sn(1)-C(19) Sn(1)-O(1) Sn(2)-O(2) 99.31(17) 124.4(2) 95.09(17) 116.5(2) 89.23(17) 117.12(19) 2.138(3) 2.494(3) 7 C(7)-Sn(1)-C(19) C(13)-Sn(1)-N(1) O(1)-Sn(1)-N(1) C(7)-Sn(1)-N(1) C(19)-Sn(1)-N(1) C(4)-O(1) C(4)-O(2) 117.12(19) 83.35(16) 177.29(14) 82.94(17) 90.02(17) 1.278(5) 1.229(5) C(2)-Sn(1)-C(3) C(2)-Sn(1)-C(1) C(3)-Sn(1)-C(1) C(2)-Sn(1)-O(1) C(3)-Sn(1)-O(1) Sn(1)-O(1) Sn(1)-O(2) Sn(1)-O(3) 123.4(2) 119.7(3) 115.4(3) 95.81(17) 97.28(18) 2.156(3) 2.444(4) 2.507(8) 8 O(1)-Sn(1)-O(2) C(1)-Sn(1)-O(1) C(2)-Sn(1)-O(2) C(3)-Sn(1)-O(2) C(13)-O(1) C(13)-O(2) 173.55(12) 89.08(18) 83.37(16) 88.47(17) 1.275(6) 1.251(6) C(5)-Sn(1)-C(1) C(5)-Sn(1)-C(9) C(1)-Sn(1)-C(9) C(5)-Sn(1)-O(1) C(1)-Sn(1)-O(1) C(9)-Sn(1)-O(1) C(9)-Sn(1)-O(3) O(1)-Sn(1)-O(3) 122.0(2) 111.3(2) 124.1(2) 89.90(17) 97.58(19) 98.43(18) 107.3(2) 131.0(2) C(5)-Sn(1)-O(2) C(1)-Sn(1)-O(2) C(9)-Sn(1)-O(2) O(1)-Sn(1)-O(2) C(5)-Sn(1)-O(3) C(1)-Sn(1)-O(3) O(2)-Sn(1)-O(3) 83.51(17) 81.73(19) 88.75(18) 171.66(13) 42.1(2) 101.1(2) 41.74(19)

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