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1 Supporting Information Wiley-VCH Weinheim, Germany
2 Crystal-to-Crystal Transformation between Three Cu(I) Coordination Polymers and Structural Evidence for Luminescence Thermochromism Tae Ho Kim 1, Yong Woon Shin 2, Jong Hwa Jung 1, Jae Sang Kim 1, and Jineun Kim 1 * 1 Department of Chemistry (BK21) and Research Institute of Natural Science, Gyeongsang National University, Jinju , S. Korea 2 Test & Analytical Laboratory, Korea Food & Drug Administration, Busan , South Korea Table of Contents: Title and table of contents S1 General S3 Scheme S1. Synthesis of 1,4-bis((methylthio)propanoyl)piperazine (L). S3 Preparations of 1, 2, 3, and 3 S4 Figure S1. Ortep diagram of L. S5 Table S1. Crystal data and structure refinement for L. S5 Figure S2. Photograph of crystals 1, 2, and 3 with/without UV irradiation. S6 Figure S3. SEM images of 1, 2, and 3. S7 Figure S4. Ortep (a) and packing (b) diagrams of 1. S8 Table S2. Crystal data and structure refinement for 1. S9 Figure S5. Ortep (a) and packing (b) diagrams of 2. S10 Table S3. Crystal data and structure refinement for 2. S11 Figure S6. Ortep (a) and packing (b) diagrams of 3. S12 Table S4. Crystal data and structure refinement for 3. S13 Figure S7. Conformation of L. S14 Figure S8. Packing arrangements of Cu 4 I 4. S14 Table S4. Bond distances of 2 at four different temperatures. S15 Table S5. Bond distances of 3 at four different temperatures. S17 Figure S9. Photoluminescence spectra of before (a) and after (b) heating at 180 C. S19 Figure S10. Powder XRD Patterns of 1. S20 Figure S11. Powder XRD Patterns of 2. S21 S1
3 Figure S12. Powder XRD Patterns of 3 (a and b) and 3 (c). S22 Figrue S13. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) traces for 1. S23 Figrue S14. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) traces for 2. S23 Figrue S15. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) traces for 3. S24 S2
4 General The 1 H and 13 C NMR spectra were recorded with a Bruker Advance-300(300 MHz) NMR spectrometer. The FT-IR spectra of the coordination polymers were measured with a Shimadzu FT-IR 8100 spectrometer. The elemental analysis was carried out on a LECO CHNS-932 elemental analyzer. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) were performed under N 2 (g) at a scan rate of 10 C min -1 using a TA SDT Q600 thermal analyzer. For field emission scanning electron microscope (FE-SEM) a piece of compounds was placed on a carbon tape after gold coating, the specimen was then examined with Philips XL30 S FEG. Scheme S1 S O OH i. SOCl 2, triethyl amine ii. triethyl amine, thiomorpholine i ii S L O N S 2-(cyclohexylthio)-1-thiomorpholinoethane (L). Thionyl chloride (2.38 g, 20.0 mmol) was added dropwise to 2-cyclohexylthioacetic acid (3.48 g, 20.0 mmol) in the pesence of triethylamine (2.02 g, 20.0 mmol) in chloroform. The mixture was refluxed for 2 h and cooled down to room temperature. Then, thiomorpholine (2.38 g, 20.0 mmol) and triethylamine (2.02 g, 20.0 mmol) in chloroform were added dropwise to the resulting acid chloride solution, cooled by salt and ice water. The solution was stirred for 2 h, and then water was added. Organic layer was collected and water layer was extr acted with chloroform. The combined organic layers dried with anhydrous sodium sulfate were evaporated to give crude oil. Column chromatography (silica gel, ethyl acetate/hexane = 20/80 (v/v), R f 0.2) gave pure product (4.18 g, 78%). 1 H NMR (300 MHz, CDCl 3 ): δ (d, 4H, CH 2 NCH 2 ), (s, 2H, COCH 2 S), (m, 1H SCH), (d, 4H, CH 2 SCH 2 ), (m, 10H, CH(CH 2 ) 5 ). 13 C NMR (75.4 MHz, CDCl 3 ): δ , 44.33, 33.39, 32.08, 27.80, 27.39, 25.92, IR(KBr, ν, cm -1 ): 2926 s, 2851 s, 1641 s, 1445 s, 1366 m, 1288 m, 1135 s, 1038 w, 999 w, 958 s, 917 m, 818 w, 738 w, 659 w. Mass spectrum m/z 259 (M, 11 %), 145 (100), 130 (25), 117 (57), 102(15), 83 (20). S3
5 Preparations of 1, 2, 3, and 3 [Cu 2 I 2 L 2 ] n (1): An acetonitrile (1 ml) solution of L (0.026 g, 0.10 mmol) was allowed to mix with an acetonitrile (1 ml) solution of CuI (0.019 g, 0.10 mmol), followed by sonication. Yellowish-colored precipitates were filtered and washed with diethyl ether/acetonitrile (1/1) solution (0.026 g, 58%). Single crystals suitable for X-ray analysis were obtained by slow evaporation. m.p C. IR(KBr, ν, cm - 1 ): 2931 s, 2852 s, 1660 s, 1424 s, 1367 m, 1287 m, 1177 s, 1039 w, 997 w, 956 s, 882 m, 817 w, 730 w, 649 w. [Cu 2 I 2 L 2 ] n Anal. Calcd. for C 24 H 42 N 2 O 2 S 4 Cu 2 I 2 : C 32.04, H 4.70, N 3.11, S Found: C 31.97, H 4.66, N 3.27, S 14.39%. [Cu 4 I 4 L 2 ] n (2): An acetonitrile (1 ml) solution of L (0.026 g, 0.10 mmol) was allowed to mix with an acetonitrile (1 ml) solution of CuI (0.038 g, 0.20 mmol), followed by diethyl ether diffusion and sonication. White precipitates were filtered and washed with diethyl ether/acetonitrile (1/1) solution (0.033 g, 52%). Single crystals suitable for X-ray analysis were obtained by diethyl ether diffusion. m.p C. IR(KBr, ν, cm -1 ): 2921 s, 2847 m, 1642 s, 1440 s, 1364 w, 1294 m, 1253 w, 1130 w, 1044 w, 960 m, 923 w, 733 w, 651 w. [Cu 4 I 4 L 2 ] n Anal. Calcd. for C 24 H 42 N 2 O 2 S 4 Cu 4 I 4 : C 22.51, H 3.31, N 2.19, S Found: C 22.33, H 3.66, N 2.14, S 9.71%. {[Cu 4 I 4 L 2 ] CH 3 CN n-c 6 H 12 } n (3) An acetonitrile (1 ml) solution of L (0.026 g, 0.10 mmol) was allowed to mix with an acetonitrile (1 ml) solution of CuI (0.038 g, 0.20 mmol), followed by diethyl ether/n- Hexane (1/1) diffusion and sonication. White precipitates were filtered and washed with diethyl ether/n- Hexane/acetonitrile (1/1/1) solution (0.044 g, 69%). Single crystals suitable for X-ray analysis were obtained from boundary surface between n-hexane and acetonitrile solution (Figure S1b). [Cu 4 I 4 L 2 ] n (3 ): 3 was obtained by desolvating the white precipitates 3 under vacuum for 1 hr. m.p C. IR(KBr, ν, cm -1 ): 2920 s, 2847 m, 1652 s, 1445 s, 1366 w, 1303 m, 1253 w, 1118 w, 1043 w, 958 m, 916 w, 729 w, 651 w. [Cu 4 I 4 L 2 ] n Anal. Calcd. for C 24 H 42 N 2 O 2 S 4 Cu 4 I 4 : C 22.51, H 3.31, N 2.19, S Found: C 22.55, H 3.46, N 2.35, S 10.29%. S4
6 Figure S1. Ortep diagram of L. Table S1. Crystal data and structure refinement for L Empirical formula C 12 H 21 NOS 2 Formula weight Temperature 173(2) K Wavelength Å Crystal system Monoclinic Space group P2(1)/c Unit cell dimensions a = (6) Å α= 90. b = (4) Å β= (10). c = (4) Å γ = 90. Volume (10) Å 3 Z 4 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) 560 Crystal size 0.35 x 0.25 x 0.15 mm 3 Theta range for data collection 2.62 to Index ranges -18<=h<=17, -11<=k<=12, -9<=l<=13 Reflections collected 8357 Independent reflections 3165 [R(int) = ] Completeness to theta = % Absorption correction Empirical ψ-scan Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 3165 / 0 / 145 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å S5
7 UV irradiation UV irradiation (b) (a) (c) Figure S2. Photograph of crystals 1, 2, and 3 with/without UV irradiation; yellow crystal 1 and white crystal 2 (top), orange luminescent 2 (bottom) (a), green luminescent 3 grown from boundary surface between n-hexane layer and acetonitrile solution (b), block crystal 2 and plate (urchin shape) crystal 3 (top), orange luminescent 2 and green luminescent 3 (bottom) (c). S6
8 (a) (b) (c) Figure S3. SEM images of 1, 2, and 3 ; rhombohedron-shape block 1 (a), hexagonalshape block 2 (b), and plate 3 (c). S7
9 (a) (b) Figure S4. Ortep (a) and packing (b) diagrams of 1. Hydrogen atoms are omitted. S8
10 Table S2. Crystal data and structure refinement for Empirical formula C 12 H 21 NOS 2 CuI Formula weight Temperature 173(2) K Wavelength Å Crystal system Monoclinic Space group P2(1)/c Unit cell dimensions a = (5) Å α= 90. b = (4) Å β= (10). c = (8) Å γ = 90. Volume (13) Å 3 Z 4 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) 888 Crystal size 0.20 x 0.16 x 0.05 mm 3 Theta range for data collection 2.00 to Index ranges -11<=h<=13, -11<=k<=9, -22<=l<=23 Reflections collected 9544 Independent reflections 3657 [R(int) = ] Completeness to theta = % Absorption correction Empirical ψ-scan Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 3657 / 0 / 163 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å S9
11 (a) (b) Figure S5. Ortep (a) and packing (b) diagrams of 2. Hydrogen atoms are omitted. S10
12 Table S3. Crystal data and structure refinement for Empirical formula C 24 H 42 N 2 O 2 S 4 Cu 4 I 4 Formula weight Temperature 173(2) K Wavelength Å Crystal system Orthorhombic Space group Pbca Unit cell dimensions a = (6) Å α= 90. b = (9) Å β= 90. c = (12) Å γ = 90. Volume (6) Å 3 Z 8 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) 4864 Crystal size 0.25 x 0.18 x 0.16 mm 3 Theta range for data collection 1.49 to Index ranges -18<=h<=17, -18<=k<=27, -35<=l<=34 Reflections collected Independent reflections 9254 [R(int) = ] Completeness to theta = % Absorption correction Empirical ψ-scan Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 9254 / 0 / 361 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å S11
13 (a) (b) Figure S6. Ortep (a) and packing (b) diagrams of 3. Hydrogen atoms and solvates are omitted. S12
14 Table S4. Crystal data and structure refinement for Empirical formula C 32 H 59 N 3 O 2 S 4 Cu 4 I 4 Formula weight Temperature 173(2) K Wavelength Å Crystal system Triclinic Space group P-1 Unit cell dimensions a = (4) Å α= (10). b = (4) Å β= (10). c = (5) Å γ = (10). Volume (13) Å 3 Z 2 Density (calculated) g/cm 3 Absorption coefficient mm -1 F(000) 1360 Crystal size 0.30 x 0.15 x 0.05 mm 3 Theta range for data collection 1.38 to Index ranges -14<=h<=15, -18<=k<=18, -20<=l<=20 Reflections collected Independent reflections [R(int) = ] Completeness to theta = % Absorption correction SADABS Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters / 28 / 471 Goodness-of-fit on F Final R indices [I>2sigma(I)] R 1 = , wr 2 = R indices (all data) R 1 = , wr 2 = Largest diff. peak and hole and e.å S13
15 (a) (b) Figure S7. Conformation of L; Syn arrangement in 2 (a), Anti arrangement in 3 (b). (a) (b) (c) (d) Figure S8. Packing arrangements of Cu 4 I 4 ; view down b-axis of 2 (a), view down a-axis of 3 (b), view down c-axis of 2 (c), view down c-axis of 3 (d). All atoms of L except S are omitted for clarity. S14
16 Table S5. Bond distances of 2 at four different temperatures. Atom1 Atom2 d-123k d-173k d-223k d-298k (d-298k) - (d-123k) C2 C C14 C Cu1 Cu Cu1 Cu C4 C N1 C Cu2 Cu Cu2 Cu C7 C Cu3 I Cu1 I Cu4 I O2 C Cu3 I Cu3 Cu C16 C Cu2 I C11 C Cu2 I Cu2 I S1 C N2 C C13 C C21 C Cu1 I C9 C Cu1 I Cu4 I Cu1 S Cu2 S Cu3 S Cu1 Cu S15
17 Cu3 I Cu4 I C23 C Cu4 S S3 C S2 C S4 C N2 C S3 C O1 C C13 C S1 C C19 C S4 C N1 C N2 C C17 C C1 C S2 C C1 C N1 C C5 C C3 C C15 C S16
18 Table S6. Bond distances of 3 at four different temperatures. Atom1 Atom2 d-123k d-173k d-223k d-298k (d-298k) - (d-123k) Cu1 I Cu3 I S1 C Cu1 Cu Cu1 Cu Cu2 Cu Cu2 I Cu2 Cu Cu3 Cu C1 C C19 C Cu1 Cu N1 C C16 C C9 C N2 C O1 C Cu4 I S2 C C13 C N2 C Cu2 I Cu3 S Cu1 S Cu4 I Cu4 S C5 C Cu4 I S3 C C7 C S3 C C23 C S17
19 Cu2 S S4 C C11 C C15 C Cu3 I S1 C N1 C C3 C O2 C C21 C S2 C Cu1 I C13 C Cu2 I C14 C C4 C N1 C C17 C N2 C S4 C C2 C C1 C Cu3 I Cu1 I S18
20 I em λ / nm (a) nm I em λ / nm (b) Figure S9. Photoluminescence spectra of before (a) and after (b) heating at 180 C. S19
21 (a) (b) Intensity (c) Theta / degree Figure S10. Powder XRD Patterns of 1; frame image (a), measured (b), and calculated (c). S20
22 (a) (b) Intensity (c) Theta / degree Figure S11. Powder XRD Patterns of 2; frame image (a), measured (b), and calculated (c). S21
23 (a) (b) Intensity (c) Theta / degree Figure S12. Powder XRD Patterns of 3 (a and b) and 3 (c); frame image (a), measured (b), and calculated (c). S22
24 Weight [%] Temperature Difference [μv / mg] Temperature [ o C] Figure S13. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) traces for 1. (black solid line : TGA, red dash line : DTA) Weight [%] Temperature Difference [μv / mg] Temperature [ o C] Figure S14. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) traces for 2. (black solid line : TGA, red dash line : DTA) S23
25 Weight [%] Temperature Difference [μv / mg] Temperature [ o C] Figure S15. Thermogravimetric analysis (TGA) and differential thermal analysis (DTA) traces for 3. (black solid line : TGA, red dash line : DTA) S24
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