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1 Supporting Information All-in-one: Achieving robust, strongly-luminescent and highlydispersible hybrid materials by combining ionic and coordinate bonds in molecular crystals Wei Liu, [a] Kun Zhu, [a] Simon J. Teat, [b] Gangotri Dey, [a] Zeqing Shen, [a] Lu Wang, [a] Deirdre M. O Ćarroll, [a][c] and Jing Li* [a] [a] Department of Chemistry and Chemical Biology, Rutgers University, 610 Taylor Road, Piscataway, NJ 08854, USA [b] Advanced Light Source Lawrence Berkeley National Laboratory, 1 Cyclotron Road, Berkeley, CA 94720, USA [c] Department of Materials Science and Engineering, Rutgers University, 607 Taylor Road, Piscataway, NJ This work is dedicated to Professor Roald Hoffmann on the occasion of his 80 th birthday. S1
2 TABLE OF CONTENT S1. Characterizations of ligands S2. Crystal images and structural plots of compounds 1-10 S3. Characterizations of compounds 1-10 S4. Optical absorption and emission spectra, luminescence decay profiles and related data S5. DFT calculation details of selective AIO type compounds S6. References S2
3 S1. Characterizations of ligands (a) (b) Figure S1. Structural plot and 1 H NMR spectrum of bz-ted. S3
4 (a) (b) Figure S2. Structural plot and 1 H NMR spectrum of pr-ted. S4
5 Figure S3. Structural plot and 1 H NMR spectrum of i-pr-ted. S5
6 (a) (b) Figure S4. Structural plot and 1 H NMR spectrum of bu-ted. S6
7 (a) (b) Figure S5. Structural plot and 1 H NMR spectrum of btm. S7
8 Figure S6. Structural plot and 1 H NMR spectrum of Cl-mbt. S8
9 (a) (b) Figure S7. Structural plot and 1 H NMR spectrum of bttmm. S9
10 (a) (b) Figure S8. Structural plot and 1 H NMR spectrum of bttmme. S10
11 (a) (b) Figure S9. Structrual plot and and 1 H NMR spectrum of btmdb. S11
12 S2. Crystal images and structural plots of compounds 1-10 Figure S10. (a) Structure plot of 1. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls. (b) Crystal image of 1. S12
13 Figure S11. (a) Structure plot of 2. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls. Cl: green balls. (b) Crystal image of 2. S13
14 Figure S12. (a) Structure plot of 3. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls. (b) Crystal image of 3. S14
15 Figure S13. (a) Structure plot of 4. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls, Br: brown balls. (b) Crystal image of 4. S15
16 Figure S14. (a) Structure plot of 5. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls. (b) Crystal image of 5. S16
17 Figure S15. (a) Structure plot of 6. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls. (b) Crystal image of 6. S17
18 Figure S16. (a) Structure plot of 7. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls, S: yellow ball. (b) Crystal image of 7. S18
19 Figure S17. (a) Structure plot of 8. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls, P: dark green balls. (b) Crystal image of 8. S19
20 Figure S18. (a) Structure plot of 9. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls, P: dark green balls. (b) Crystal image of 9. S20
21 Figure S19. (a) Structure plot of 10. Cu: cyan balls, I: purple balls, N: blue balls, C: grey balls. (b) Crystal image of 10. S21
22 Table S1. Shortest Cu-Cu distances in compounds 1-9. Structure Cu-Cu distance (Å) Cu 3 I 5 (bz-ted) 2 (1) 2.61, 2.66 Cu 4 I 6 (3-Cl-pr-ted) 2 (2) 2.56, 2.74 Cu 4 I 6 (pr-ted) 2 (3) 2.64, 2.70 Cu 4 I 6 (2-Br-et-ted) 2 (4) 2.64 Cu 5 I 7 (i-pr-ted) 2 (5) 2.71, 2.72 Cu 6 I 8 (bu-ted) 2 (6) 2.61, 2.71 Cu 2 I 4 (mtp) 2 (7) 2.86 Cu 4 I 6 (tpp) 2 (bttmm) 2 (8) 3.01, 3.29 Cu 4 I 6 (tpp) 2 (btmdme) 2 (9) 3.06 S22
23 S3. Characterizations of compounds 1-10 Figure S20a. PXRD patterns of compound 1-5. From bottom to top: simulated 1, as made 1, simulated 2, as made 2, simulated 3, as made 3, simulated 4, as made 4, simulated 5, as made 5. S23
24 Figure S20b. PXRD patterns of compound From bottom to top: simulated 6, as made 6, simulated 7, as made 7, simulated 8, as made 8, simulated 9, as made 9, simulated 10, as made 10. S24
25 Figure S21. PXRD patterns of simulated 3 (black) and its film after annealing (red). S25
26 Figure S22. TG plots of structures in sub group (I). 1 (black), 2 (red), 3 (blue), 4 (green), 5 (pink), 6 (gold). S26
27 Figure S23. TG plots of structures in sub group (II). 7 (black), 8 (red), 9 (blue), 10 (green). S27
28 S4. Optical absorption and emission spectra, luminescence decay profiles and related data Figure S24. Optical absorption spectra of compounds in sub group (I). 1 (black), 2 (red), 3 (blue), 4 (green), 5 (pink), 6 (green-yellow). S28
29 Figure S25. Optical absorption spectra of compounds in sub group (II). 7 (black), 8 (red), 9 (blue), 10 (green). S29
30 Figure S26. Excitation and emission spectra of compounds Solid line: emission spectra, λ ex = 360 nm; dotted line: excitation spectra. From bottom to top: S30
31 Figure S27. (a) Luminesence decay profiles of 3 at various temperatures (λ ex = 380 nm). (b) Single exponential decay curves fit to the data in (a) using a single (i.e., first-order) exponential decay function. Table S2. Lifetime values of 3 at various temperatures obtained from fits to the luminescence decay profiles using a single (i.e., first-order) exponential decay function. Temperature Lifetime (μs) (K) S31
32 Figure S28. (a) Luminesence decay profiles of 6 at various temperatures (λ ex = 380 nm). (b) Single exponential decay curves fit to the data in (a) using a single (i.e., first-order) exponential decay function. Table S3. Lifetime values of 6 at various temperatures obtained from fits to the luminescence decay profiles using a single (i.e., first-order) exponential decay function. Temperature Lifetime (μs) (K) S32
33 Table S4. Lifetime values of 8 at various temperatures. The lifetime values were obtained from fits to the luminescence decay profiles using a double (i.e., second-order) exponential decay function. 1 and 2 are the lifetime decay constants extracted from the double exponential decay fit function. Temperature (K) Average Amplitude Weighted (μs) 1 (μs) (20.3%) (17.0%) (19.7%) (20.1%) (48.6%) 2 (μs) (79.7%) (83.0%) 6.76 (80.3%) 3.14 (69.9%) 2.16 (51.4%) S33
34 Figure S29. (a) Luminesence decay profiles of 10 at various temperatures (λ ex = 380 nm). (b) Double exponential decay curves fit to the data in (a) using a double (i.e., second-order) exponential decay function. Table S5. Lifetime values of 10 at various temperatures. The lifetime values were obtained from fits to the luminescence decay profiles using a double (i.e., second-order) exponential decay function. 1 and 2 are the lifetime decay constants extracted from the double exponential decay fit function. Temperature (K) Average Amplitude 1 (μs) 2 (μs) Weighted (μs) (13.5%) (86.5%) (24.3%) (75.7%) (12.3%) 6.64 (87.7%) (31.2%) 2.57 (68.2%) (29.9%) 2.09 (70.1%) S34
35 Figure S30. Emission spectra of 10 at various temperatures (λ ex = 380 nm). S35
36 Figure S30a. PL emission spectra of 3 (top) and 8 (bottom) at room temeprature (black), 80 C (red) and 150 C (blue). (λ ex = 360 nm). S36
37 Table S6. Summary of luminescence and thermal properties of pure ionic compounds Structure Luminescence λ em (nm) IQY (%, λ = 360 nm) T D ( C) CuI 2 (1,4-dm-ted) 1 None N.A. N.A Cu 4 I 8 (1,4-de-ted) 2 Very weak Cu 4 I 4 Br 4 (1,4-de-ted) 2 Very weak Cu 4 I 4 Br 4 (4,4 -db-1,4-de-ted) 2 Very weak Cu 3 I 6 (1,4-db-ted) 1.5 Weak CuI 2 (1-me-py) 4 Almost none Cu 2 I 3 (1-me-py) 5 Weak CuI 2 (1,1 -de-bpy) 0.5 None N.A. N.A CuI 3 (1,1 -dp-bpy) 0.5 None N.A. N.A CuI 2 (4,4 -pr-bpp) 0.5 None N.A. N.A CuI 3 (1-pr-qui) 2 None N.A. N.A ,4-dm-ted = 1,4-dimethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium 1,4-de-ted = 1,4-diethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium 4,4 -db-1,4-de-ted = 4,4'-(butane-1,4-diyl)bis(1-ethyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium) 1,4-db-ted = 1,4-dibutyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium 1-me-py = 1-methylpyridin-1-ium 1,1 -de-bpy = 1,1'-diethyl-[4,4'-bipyridine]-1,1'-diium 1,1 -de-bpy = 1,1'-dipropyl-[4,4'-bipyridine]-1,1'-diium 4,4 -pr-bpp = 4,4'-(propane-1,3-diyl)bis(1-methylpyridin-1-ium) 1-pr-qui = 1-propylquinolin-1-ium S37
38 Figure S31. Schematic showing the design of prototype LED lighting devices. Figure S32. A paper banner coated with AIO phosphors of four different colors (under UV irradiation). S38
39 S5. DFT calculation details of selective AIO type compounds Figure S33. Density of states (DOS) plots for compounds 3. Color scheme: Black dash: total; cyan: Cu (3d); pink: Cu (4s); red: I (5p); purple: I (5d). Figure S34. Density of states (DOS) plots for compounds 8. Color scheme: Black dash: total; cyan: Cu (3d); red: I (5p); purple: I (5d); blue: N (2p); black: C (2p). S39
40 Table S7. Calculated and experimentally estimated band gap values for selected AIO type compounds. Compound Calculated B.G. (ev) Experimental B.G. (ev) Cu 4 I 6 (pr-ted) 2 (3) Cu 5 I 7 (i-pr-ted) 2 (5) Cu 2 I 4 (mtp) 2 (7) Cu 4 I 6 (tpp) 2 (bttmm) 2 (8) Table S8. Main contributions from atomic orbitals to the valence band maximum (VBM) region (energy range: 0.5 ev). atomic orbital compound Cu 4 I 6 (pr-ted) 2 (3) Cu 5 I 7 (i-pr-ted) 2 (5) Cu 2 I 4 (mtp) 2 (7) Cu 4 I 6 (tpp) 2 (bttmm) 2 (8) VBM (ev) ~ ~ ~ ~ -0.9 Cu(3d) 54.6% 56.5% 47.0% 51.3% I(5p) 18.4% 29.1% 31.4% 32.6% Cu(4p) 7.2% 1.2% 1.2% 3.4% I(5d) 6.7% 3.0% 4.7% 6.3% S40
41 Table S9. Main contributions from atomic orbitals to the conduction band minimum (CBM) region (energy range: 0.5 ev). compound atomic orbital Cu 4 I 6 (pr-ted) 2 (3) Cu 5 I 7 (i-pr-ted) 2 (5) Cu 2 I 4 (mtp) 2 (7) Cu 4 I 6 (tpp) 2 (bttmm) 2 (8) CBM (ev) 1.15 ~ ~ ~ ~ 1.4 I(5d) 14.3% 8.8% 2.7% 3.6% Cu(4s) 2.4% 0.5% 0.5% 0.8% I(5p) 20.4% 17.3% 3.0% 3.3% N(2s) 0.2% 0.0% 0.0% 0.5% C(2p) 1.2% 0.4% 56.6% 28.8% N(2p) 0.2% 0.1% 17.7% 46.4% Cu(4p) 16.5% 4.4% 0.3% 2.4% Cu(3d) 35.0% 60.0% 1.9% 7.6% S6. Reference (1) Hou, J.-J.; Li, S.-L.; Li, C.-R.; Zhang, X.-M. Dalton Trans. 2010, 39, (2) Xin, B.; Li, Y.; Zeng, G.; Peng, Y.; Li, G.; Shi, Z.; Feng, S. Z. Naturforsch. B 2013, 639, 611. (3) Li, S.-L.; Zhang, F.-Q.; Zhang, X.-M. Chem. Commun. 2015, 51, (4) Adam, D.; Herrschaft, B.; Hartl, H. In Zeitschrift für Naturforschung B 1991; Vol. 46, p 738. (5) Hou, Q.; Xu, J.-N.; Yu, J.-H.; Wang, T.-G.; Yang, Q.-F.; Xu, J.-Q. J. Solid State Chem. 2010, 183, (6) Chan, H.; Chen, Y.; Dai, M.; Lu, C.-N.; Wang, H.-F.; Ren, Z.-G.; Huang, Z.-J.; Ni, C.-Y.; Lang, J.-P. CrystEngComm 2012, 14, 466. (7) Chen, Y.; Yang, Z.; Wu, X.-Y.; Ni, C.-Y.; Ren, Z.-G.; Lang, J.-P. Phys Chem Chem Phys. 2011, 13, (8) Jiao, X.; Niu, Y.; Zhang, H.; Zhu, L.; Zhao, F. J. Chem. Crystallogr. 2006, 36, 685. (9) Wang, Y. J.; Li, H. H.; Chen, Z. R.; Huang, C. C.; Liu, J. B. Acta Crystallogr., Sect. E 2007, 63, m2736. S41
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