Supporting Information. Crystal structures, magnetic and electrochemical properties of. coordination polymers based on the
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1 Supporting Information Crystal structures, magnetic and electrochemical properties of coordination polymers based on the tetra(4-pyridyl)-tetrathiafulvalene ligand Hai-Ying Wang, Yue Wu, Chanel F. Leong, Deanna M. D'Alessandro and Jing-Lin Zuo *, State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Advanced Microstructures, Nanjing University, Nanjing , P. R. China School of Chemistry, The University of Sydney, New South Wales 2006, Australia * To whom correspondence should be addressed. zuojl@nju.edu.cn. 1
2 1. Materials and Measurements All the starting materials were commercially available and were used as received unless otherwise stated. The TTF(py) 4 ligand was synthesized according to the literature method. S1 The Bruker D8 Advance X-ray diffractometer equipped with Cu-Kα radiation (λ = Å) was used to collect powder X-ray diffraction (PXRD) data at room temperature. Infrared absorption spectra of compounds 1-7 were recorded on a Vector27 Bruker Spectrophotometer with KBr pellets in the range of cm -1. C, H, N and S analyses were carried out on a Perkin-Elmer 240C analyzer. Thermogravimetric analyses (TGA) were performed using a STA 449C thermal analysis system with a heating rate of 10 C/min under N 2 conditions. Magnetic susceptibilities for polycrystalline samples were measured with the use of a Quantum Design MPMS-SQUID-VSM magnetometer in the temperature range K. Field dependences of magnetization were measured using a Quantum Design MPMS-SQUID-VSM system in an applied field up to 70 koe. Cyclic voltammetry measurements were performed in n-bu 4 NPF 6 /CH 3 CN electrolyte using a BAS Epsilon electrochemical analyser and three electrode system. All potentials are reported in mv versus Fc/Fc + couple. Nitrogen (N 2, at 77 K) and carbon dioxide (CO 2, at 195 K) sorption experiments were measured on the Micromeritics ASAP 2020 instrument. Reference (S1) Vajpayee, V.; Bivaud, S.; Goeb, S.; Croue, V.; Allain, M.; Popp, B. V.; Garci, A.; Therrien, B.; Salle, M. Organometallics 2014, 33,
3 2.TableS1: selected bond lengths (Å) and angles ( ) for compounds 1-7. compound 1 Cu(1)-N(2)# (4) Cu(1)-O(2)# (4) Cu(1)-N(2) 2.013(4) Cu(1)-O(1) 2.155(4) Cu(1)-O(2) 2.078(4) Cu(1)-O(1)# (4) N(2)#2-Cu(1)-N(2) 180.0(3) O(2)-Cu(1)-O(1) 92.22(17) N(2)#2-Cu(1)-O(2) 90.08(16) O(2)#2-Cu(1)-O(1) 87.78(17) N(2)-Cu(1)-O(2) 89.92(16) N(2)#2-Cu(1)-O(1)# (16) N(2)#2-Cu(1)-O(2)# (16) N(2)-Cu(1)-O(1)# (16) N(2)-Cu(1)-O(2)# (16) O(2)-Cu(1)-O(1)# (17) O(2)-Cu(1)-O(2)# (4) O(2)#2-Cu(1)-O(1)# (17) N(2)#2-Cu(1)-O(1) 89.43(16) O(1)-Cu(1)-O(1)# (2) N(2)-Cu(1)-O(1) 90.57(16) compound 2 Co(1)-O(1)# (2) Co(1)-N(2) 2.221(3) Co(1)-O(1) 2.030(2) Co(2)-O(4) 2.034(3) Co(1)-O(3)# (3) Co(2)-O(4)# (3) Co(1)-O(3) 2.041(3) Co(2)-O(2)# (2) Co(1)-N(2)# (3) Co(2)-O(2) 2.040(2) O(1)#2-Co(1)-O(1) (1) Co(2)-N(1)# (3) O(1)#2-Co(1)-O(3)# (11) O(3)-Co(1)-N(2) 90.09(11) O(1)-Co(1)-O(3)# (11) N(2)#2-Co(1)-N(2) (1) O(1)#2-Co(1)-O(3) 91.21(11) O(4)-Co(2)-O(4)# (12) O(1)-Co(1)-O(3) 88.79(11) O(4)-Co(2)-O(2)# (10) O(3)#2-Co(1)-O(3) (1) O(4)#3-Co(2)-O(2)# (10) O(1)#2-Co(1)-O(1) (1) O(4)-Co(2)-O(2) 89.95(10) O(1)#2-Co(1)-N(2)# (10) O(4)#3-Co(2)-O(2) 90.05(10) O(1)-Co(1)-N(2)# (10) O(2)#3-Co(2)-O(2) (14) O(3)#2-Co(1)-N(2)# (11) O(4)-Co(2)-N(1)# (11) O(3)-Co(1)-N(2)# (11) O(4)#3-Co(2)-N(1)# (11) O(1)#2-Co(1)-N(2) 90.98(10) O(2)#3-Co(2)-N(1)# (10) O(1)-Co(1)-N(2) 89.02(10) O(2)-Co(2)-N(1)# (10) O(3)#2-Co(1)-N(2) 89.91(11) O(4)-Co(2)-N(1) 87.14(11) O(4)#3-Co(2)-N(1) 92.86(11) O(2)-Co(2)-N(1) 90.11(10) O(2)#3-Co(2)-N(1) 89.89(10) N(1)#3-Co(2)-N(1) 180 compound 3 Mn(1)-O(3) 2.150(2) Mn(2)-O(1) 2.156(2) Mn(1)-O(3)# (2) Mn(2)-O(1)# (2) Mn(1)-O(4) 2.155(2) Mn(2)-O(2)# (2) Mn(1)-O(4)# (2) Mn(2)-O(2) 2.170(2) Mn(1)-N(1) 2.275(2) Mn(2)-N(2)# (3) Mn(1)-N(1)# (2) Mn(2)-N(2) 2.289(3) 3
4 O(3)-Mn(1)-O(3)# (11) O(3)-Mn(1)-N(1)# (9) O(3)-Mn(1)-O(4) 84.28(8) O(3)#2-Mn(1)-N(1)# (9) O(3)#2-Mn(1)-O(4) 95.72(8) O(4)-Mn(1)-N(1)# (8) O(3)-Mn(1)-O(4)# (8) O(4)#2-Mn(1)-N(1)# (9) O(3)#2-Mn(1)-O(4)# (8) N(1)-Mn(1)-N(1)# (1) O(4)-Mn(1)-O(4)# (1) O(1)-Mn(2)-O(1)# (9) O(3)-Mn(1)-N(1) 84.99(9) O(1)-Mn(2)-O(2)# (8) O(3)#2-Mn(1)-N(1) 95.01(9) O(1)#3-Mn(2)-O(2)# (8) O(4)-Mn(1)-N(1) 89.72(9) O(1)-Mn(2)-O(2) 82.48(8) O(4)#2-Mn(1)-N(1) 90.28(8) O(1)#3-Mn(2)-O(2) 97.52(8) O(2)#3-Mn(2)-O(2) (10) O(1)#3-Mn(2)-N(2)# (9) O(1)-Mn(2)-N(2)# (9) O(2)#3-Mn(2)-N(2)# (9) O(2)-Mn(2)-N(2)# (9) O(2)#3-Mn(2)-N(2) 91.02(9) O(1)-Mn(2)-N(2) 91.82(9) O(2)-Mn(2)-N(2) 88.98(9) O(1)#3-Mn(2)-N(2) 88.18(9) N(2)#3-Mn(2)-N(2) (13) compound 4 Cu(1)-O(7) O(5)-Cu(1)-N(2)# Cu(1)-O(3) O(7)-Cu(1)-Cu(2) 84.8 Cu(1)-O(1) O(3)-Cu(1)-Cu(2) 85.6 Cu(1)-O(5) O(1)-Cu(1)-Cu(2) 83.5 Cu(1)-N(2)# O(5)-Cu(1)-Cu(2) 83 Cu(1)-Cu(2) 2.6 N(2)#2-Cu(1)-Cu(2) Cu(2)-O(6) O(6)-Cu(2)-O(4) 90.1 Cu(2)-O(4) O(6)-Cu(2)-O(2) Cu(2)-O(2) O(4)-Cu(2)-O(2) 90 Cu(2)-O(8) O(6)-Cu(2)-O(8) 89.6 Cu(2)-N(1) 2.14 O(4)-Cu(2)-O(8) N(2)-Cu(1)# O(2)-Cu(2)-O(8) 88.3 O(7)-Cu(1)-O(3) O(6)-Cu(2)-N(1) 95.9 O(7)-Cu(1)-O(1) 88.1 O(4)-Cu(2)-N(1) 96 O(3)-Cu(1)-O(1) 89.2 O(2)-Cu(2)-N(1) 92.8 O(7)-Cu(1)-O(5) 90.4 O(8)-Cu(2)-N(1) 96.7 O(3)-Cu(1)-O(5) 90 O(6)-Cu(2)-Cu(1) 85.9 O(1)-Cu(1)-O(5) O(4)-Cu(2)-Cu(1) 83.1 O(7)-Cu(1)-N(2)# O(2)-Cu(2)-Cu(1) 85.4 O(3)-Cu(1)-N(2)# O(8)-Cu(2)-Cu(1) 84.2 O(1)-Cu(1)-N(2)#2 100 compound 5 Mn(1)-N(3)# (13) Mn(1)-N(1)# (13) Mn(1)-N(3) 2.172(13) Mn(1)-N(1) 2.304(13) Mn(1)-N(2)# (12) N(2)-Mn(1)# (12) Mn(1)-N(2)# (12) N(3)#2-Mn(1)-N(1)#2 91.1(4) N(3)#2-Mn(1)-N(3) 180.0(7) N(3)-Mn(1)-N(1)#2 88.9(4) N(3)#2-Mn(1)-N(2)#3 88.4(5) N(2)#3-Mn(1)-N(1)#2 84.5(4) 4
5 N(3)-Mn(1)-N(2)#3 91.6(5) N(2)#4-Mn(1)-N(1)#2 95.5(4) N(3)#2-Mn(1)-N(2)#4 91.6(5) N(3)#2-Mn(1)-N(1) 88.9(4) N(3)-Mn(1)-N(2)#4 88.4(5) N(3)-Mn(1)-N(1) 91.1(4) N(2)#3-Mn(1)-N(2)# (6) N(2)#3-Mn(1)-N(1) 95.5(4) compound 6 Cl(1)-Mn(1) 2.465(4) N(3)-Mn(1)-N(5)#2 89.3(4) Mn(1)-N(3) 2.198(10) N(2)#1-Mn(1)-N(5)# (4) Mn(1)-N(2)# (12) N(1)-Mn(1)-N(5)#2 92.2(4) Mn(1)-N(1) 2.291(10) N(3)-Mn(1)-N(4)#3 84.4(4) Mn(1)-N(5)# (11) N(2)#1-Mn(1)-N(4)#3 95.8(4) Mn(1)-N(4)# (10) N(1)-Mn(1)-N(4)# (4) N(2)-Mn(1)# (12) N(5)#2-Mn(1)-N(4)#3 86.5(3) N(4)-Mn(1)# (10) N(3)-Mn(1)-Cl(1) 175.9(2) N(5)-Mn(1)# (11) N(2)#1-Mn(1)-Cl(1) 91.5(3) N(3)-Mn(1)-N(2)#1 90.4(4) N(1)-Mn(1)-Cl(1) 91.5(3) N(3)-Mn(1)-N(1) 92.3(4) N(5)#2-Mn(1)-Cl(1) 89.0(3) N(2)#1-Mn(1)-N(1) 85.5(4) N(4)#3-Mn(1)-Cl(1) 91.7(3) compound 7 Cu(1)-N(7) 2.011(4) Cu(2)-N(8) 2.033(5) Cu(1)-N(4)# (5) Cu(2)-N(2)# (5) Cu(1)-N(5) 2.053(4) N(2)-Cu(2)# (5) Cu(1)-N(1) 2.058(4) N(3)-Cu(2)# (4) Cu(2)-N(6) 1.988(4) N(4)-Cu(1)# (5) Cu(2)-N(3)# (4) N(6)-Cu(2)-N(3)# (18) N(7)-Cu(1)-N(4)# (18) N(6)-Cu(2)-N(8) (17) N(7)-Cu(1)-N(5) (17) N(3)#4-Cu(2)-N(8) (18) N(4)#3-Cu(1)-N(5) (17) N(6)-Cu(2)-N(2)# (18) N(7)-Cu(1)-N(1) (18) N(3)#4-Cu(2)-N(2)# (17) N(4)#3-Cu(1)-N(1) 98.96(17) N(8)-Cu(2)-N(2)# (19) N(5)-Cu(1)-N(1) (17) Symmetry codes: complex 1: #1 -x,-y,-z+1; #2 -x+2,-y,-z; complex 2: #1 -x,-y+2,-z; #2 -x+2,-y+2,-z+1; #3 -x+2,-y+1,-z; complex 3: #1 -x,-y+2,-z; #2 -x+2,-y+2,-z+1; #3 -x+2,-y+1,-z; complex 4: #1 -x,-y+2,-z; #2 x+2,y-1/2,-z+1/2; #3 -x+2,y+1/2,-z+1/2; complex 5: #1 -x,-y+2,-z; #2 -x+1,-y+1,-z; #3 -x+1,-y+2,-z; #4 x,y-1,z; #5 x,y+1,z; complex 6: #1 x+1,y,z; #2 -x+1/2,-y,z+1/2; #3 -x+3/2,-y,z+1/2; #4 x-1,y,z; #5 -x+3/2,-y,z-1/2; #6 -x+1/2,-y,z-1/2 complex 7: #1 -x+1,-y,-z+1; #2 -x+2,-y,-z; #3 -x,-y,-z; #4 x+3/2,-y+1/2,z+1/2; #5 -x+3/2,y-1/2,-z+1/2; #6 -x+3/2,y+1/2,-z+1/2; #7 x-3/2,-y+1/2,z-1/2. 5
6 3. Table S2: The result of TOPOS 4.0 professional. ##################################### 7:C57.50 H41.50 Cl7 Cu2 N9.50 O8 S8_1 ##################################### Topology for Sc Atom Sc1 links by bridge ligands and has Common vertex with R(A-A) Cu ( 0 1 1) 9.107A 1 Cu ( 0-1 1) 9.109A 1 Cu ( 0-1 1) 9.279A 1 Cu (-1 1 0) 9.303A 1 Topology for Sc Atom Sc2 links by bridge ligands and has Common vertex with R(A-A) Cu ( 0 1 1) 9.301A 1 Cu ( 1-1 0) 9.301A 1 Cu ( 1 1 1) 9.334A 1 Cu ( 0-1 0) 9.334A 1 Topology for Sc Atom Sc3 links by bridge ligands and has Common vertex with R(A-A) Cu ( 0 1 0) 9.316A 1 Cu ( 0-1 0) 9.316A 1 Cu ( 1 1 0) 9.348A 1 Cu (-1-1 0) 9.348A 1 Topology for Cu Atom Cu1 links by bridge ligands and has Common vertex with R(A-A) Sc ( 0 1 1) 9.107A 1 Sc ( 0 1-1) 9.279A 1 Sc ( 0 1 0) 9.334A 1 Sc ( 1 1 0) 9.348A 1 Topology for Cu Atom Cu2 links by bridge ligands and has Common vertex with R(A-A) 6
7 Sc ( 0 0 1) 9.109A 1 Sc (-1 1 0) 9.301A 1 Sc ( 0 1-1) 9.303A 1 Sc ( 0 1 0) 9.316A Sc1 Point (Schlafli) symbol:{4^2;8^4} Extended point symbol:[4.4.8(2).8(2).8(8).8(8)] Sc2 Point (Schlafli) symbol:{4^2;8^4} Extended point symbol:[4.4.8(2).8(2).8(8).8(8)] Sc3 Point (Schlafli) symbol:{4^2;8^4} Extended point symbol:[4.4.8(2).8(2).8(8).8(8)] Cu1 Point (Schlafli) symbol:{4^2;8^4} Extended point symbol:[4.4.8(7).8(7).8(7).8(7)] Cu2 Point (Schlafli) symbol:{4^2;8^4} Extended point symbol:[4.4.8(7).8(7).8(7).8(7)] Point (Schlafli) symbol for net: {4^2;8^4} 4-c net; 2-nodal net Topological type: pts PtS, Cooperite; sqc183 {4^2;8^4} - VS [4.4.8(7).8(7).8(7).8(7)] [4.4.8(2).8(2).8(8).8(8)] (66909 types in 9 databases) Elapsed time: 5.81 sec. 4. The nonclassical hydrogen bonding interactions in 3 and 4. Figure S1. the three-dimensional framework formed through the nonclassical hydrogen bonds in 3 7
8 Figure S2. (top) two-dimensional layer (bottom) the nonclassical hydrogen bonding interactions in Coordination modes and conformations of the TTF(py)4 ligand in compounds 1-7 Figure S3. Coordination modes and conformations of the TTF(py)4 ligand in compounds 1-7. Hydrogen atoms have been removed for clarity. 8
9 6. TGA curves of compound 1, 4 and 7 under N 2 atmosphere. Figure S4. TGA curves of compound 1, 4, 7 under N 2 atmosphere. 7. Gas sorption isotherms for 7 and powder X-ray diffraction (PXRD) pattern. Figure S5. Gas sorption isotherms at low temperature (N 2 at 77 K, CO 2 at 195 K) and powder X-ray diffraction (PXRD) pattern for 7. 9
10 8. Powder X-ray diffraction (PXRD) patterns of compound 1-3, and 5-7 (1) Powder X-ray diffraction (PXRD) patterns of compound 1. (2) Powder X-ray diffraction (PXRD) patterns of compound 2. (3) Powder X-ray diffraction (PXRD) patterns of compound 3. 10
11 (4) Powder X-ray diffraction (PXRD) patterns of compound 5. (5) Powder X-ray diffraction (PXRD) patterns of compound 6. (6) Powder X-ray diffraction (PXRD) patterns of compound 7. Figure S6. Powder X-ray diffraction (PXRD) patterns of compounds 1-3, and
12 9. CV of 1, 2, 3 and 5. (1) Solid state CV of 1 scanning over 2 cycles at 100 mv/s where the forward scan is in the (a) anodic and (b) cathodic directions. (c) Single scan CVs of 1 over multiple scan rates are shown. Measurements were performed in 0.1 M TBAPF 6 /CH 3 CN electrolyte and were referenced to Fc/Fc +. Arrow indicates the direction of forward scan. (2) Solid state CV of 2 measured over (a) 5 cycles at 100 mv/s and (b) one scan at various different 12
13 scan rates. Measurements were performed in 0.1 M TBAPF 6 /CH 3 CN electrolyte and were referenced to Fc/Fc +. Arrow indicates the direction of forward scan. (3) Solid state CV of 3 over (a) 3 cycles at 100 mv/s and (b) multiple scan rates. Measurements were performed in 0.1 M TBAPF 6 /CH 3 CN electrolyte and were referenced to Fc/Fc +. Arrow indicates the direction of forward scan. (4) Solid state CV of 5 collected over (a) 2 successive cycles at 100 mv/s and (b) multiple scan rates. Measurements were performed in 0.1 M TBAPF 6 /CH 3 CN electrolyte and were referenced to Fc/Fc +. Arrow indicates the direction of forward scan. Asterisk marks the presence of O 2 impurity in the electrochemical cell. Figure S7. CV of 1, 2, 3 and 5. 13
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