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1 Supporting Information Tuning of Excited-State Intramolecular Proton Transfer (ESIPT) Fluorescence of Imidazo[1,2-a]pyridine in Rigid Matrices by Substitution Effect Toshiki Mutai,* irotaka Sawatani, Toshihide Shida, ideaki Shono, and Koji Araki* Department of Materials and Environmental Science, Institute of Industrial Science, the University of Tokyo, 4-6-1, Komaba, Meguro-ku, Tokyo , Japan. Contents: Table S1. Calculated energy level of M IPT and LUM IPT, and the lowest transition energy (ΔE) obtained using the CIS-method in the intramolecular hydrogen-transferred (IPT) state of Page S1 Gaussian job files for geometry optimization and energy calculation of the ESIPT state of Figure S1 S26. 1 MR (400 Mz) and 13 C MR (100 Mz) spectra of 2 14 in CDCl S2 S15... S16 S41
2 Table S1. Calculated energy level of M IPT and LUM IPT, and the lowest transition energy (ΔE) obtained using the CIS-method in the intramolecular hydrogen-transferred (IPT) state of M IPT /ev LUM IPT /ev ΔE /ev S1
3 Gaussian job file of PIP (1) %chk=1_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 1_ESIPT_ptimization C C C C C C C C C C C C C Link1-- %chk=1_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 1_ESIPT_ptimized_SinglePoint S2
4 Gaussian job file of 5 -methoxy PIP (2) %chk=2_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 2_ESIPT_ptimization C C C C C C C C C C C C C C Link1-- %chk=2_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 2_ESIPT_ptimized_SinglePoint S3
5 Gaussian job file of 5 -methyl PIP (3) %chk=3_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 3_ESIPT_ptimization C C C C C C C C C C C C C C Link1-- %chk=3_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 3_ESIPT_ptimized_SinglePoint S4
6 Gaussian job file of 5 -chloro PIP (4) %chk=4_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 4_ESIPT_ptimization C C C C C C C C C C C C C Cl Link1-- %chk=4_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 4_ESIPT_ptimized_SinglePoint S5
7 Gaussian job file of 5 -bromo PIP (5) %chk=5_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 5_ESIPT_ptimization C C C C C C C C C C C C C Br Link1-- %chk=5_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 5_ESIPT_ptimized_SinglePoint S6
8 Gaussian job file of 5 -fluoro PIP (6) %chk=6_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 6_ESIPT_ptimization C C C C C C C C C C C C C F Link1-- %chk=6_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 6_ESIPT_ptimized_SinglePoint S7
9 Gaussian job file of 6-methyl PIP (7) %chk=7_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 7_ESIPT_ptimization C C C C C C C C C C C C C C Link1-- %chk=7_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 7_ESIPT_ptimized_SinglePoint S8
10 Gaussian job file of 6-chloro PIP (8) %chk=8_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 8_ESIPT_ptimization C C C C C C C C C C C C C Cl Link1-- %chk=8_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 8_ESIPT_ptimized_SinglePoint S9
11 Gaussian job file of 6-bromo PIP (9) %chk=9_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 9_ESIPT_ptimization C C C C C C C C C C C C C Br Link1-- %chk=9_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 9_ESIPT_ptimized_SinglePoint S10
12 Gaussian job file of 6-trifluoromethyl PIP (10) %chk=10_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 10_ESIPT_ptimization C C C C C C C C C C C C C C F F F Link1-- %chk=10_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 10_ESIPT_ptimized_SinglePoint S11
13 Gaussian job file of 6-cyano PIP (11) %chk=11_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 11_ESIPT_ptimization C C C C C C C C C C C C C C Link1-- %chk=11_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 11_ESIPT_ptimized_SinglePoint S12
14 Gaussian job file of 4 -methoxy PIP (12) %chk=12_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 12_ESIPT_ptimization C C C C C C C C C C C C C C Link1-- %chk=12_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 12_ESIPT_ptimized_SinglePoint S13
15 Gaussian job file of 6-chloro-5 -methyl PIP (13) %chk=13_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 13_ESIPT_ptimization C C C C C C C C C C C C C Cl C Link1-- %chk=13_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 13_ESIPT_ptimized_SinglePoint S14
16 Gaussian job file of 5 -methyl-6-trifluoromethyl PIP (14) %chk=14_ipt_ex_pt.chk # opt cis/6-31g(d) nosymm fchk Density=All FChk=All Pop=Regular 14_ESIPT_ptimization C C C C C C C C C C C C C F C F C F Link1-- %chk=14_ipt_ex_pt.chk # cis=direct/6-31+g(d) nosymm geom=check Density=CI FChk=All Pop=Regular 14_ESIPT_ptimized_SinglePoint S15
17 2 C 3 5 -Methoxy PIP (2) Figure S1. 1 MR spectrum (CDCl 3, 400 Mz) of 2.
18 C 3 5 -Methoxy PIP (2) Figure S2. 13 C MR spectrum (CDCl 3, 100 Mz) of 2.
19 C 3 5 -Methyl PIP (3) Figure S3. 1 MR spectrum (CDCl 3, 400 Mz) of 3.
20 C 3 5 -Methyl PIP (3) Figure S4. 13 C MR spectrum (CDCl 3, 100 Mz) of 3.
21 2 Cl 5 -Chloro PIP (4) Figure S5. 1 MR spectrum (CDCl 3, 400 Mz) of 4.
22 Cl 5 -Chloro PIP (4) Figure S6. 13 C MR spectrum (CDCl 3, 100 Mz) of 4.
23 Br 5 -Bromo PIP (5) Figure S7. 1 MR spectrum (CDCl 3, 400 Mz) of 5.
24 Br 5 -Bromo PIP (5) Figure S8. 13 C MR spectrum (CDCl 3, 100 Mz) of 5.
25 2 F 5 -Fluoro PIP (6) Figure S9. 1 MR spectrum (CDCl 3, 400 Mz) of 6.
26 F 5 -Fluoro PIP (6) Figure S C MR spectrum (CDCl 3, 100 Mz) of 6.
27 2 C 3 6-Methyl PIP (7) Figure S11. 1 MR spectrum (CDCl 3, 400 Mz) of 7.
28 C 3 6-Methyl PIP (7) Figure S C MR spectrum (CDCl 3, 100 Mz) of 7.
29 2 Cl 6-Chloro PIP (8) Figure S13. 1 MR spectrum (CDCl 3, 400 Mz) of 8.
30 Cl 6-Chloro PIP (8) Figure S C MR spectrum (CDCl 3, 100 Mz) of 8.
31 2 Br 6-Bromo PIP (9) Figure S15. 1 MR spectrum (CDCl 3, 400 Mz) of 9.
32 Br 6-Bromo PIP (9) Figure S C MR spectrum (CDCl 3, 100 Mz) of 9.
33 2 CF 3 6-Trifluoromethyl PIP (10) Figure S17. 1 MR spectrum (CDCl 3, 400 Mz) of 10.
34 CF 3 6-Trifluoromethyl PIP (10) Figure S C MR spectrum (CDCl 3, 100 Mz) of 10.
35 2 C 6-Cyano PIP (11) Figure S19. 1 MR spectrum (CDCl 3, 400 Mz) of 11.
36 C 6-Cyano PIP (11) Figure S C MR spectrum (CDCl 3, 100 Mz) of 11.
37 2 C 3 4 -Methoxy PIP (12) Figure S21. 1 MR spectrum (CDCl 3, 400 Mz) of 12.
38 C 3 4 -Methoxy PIP (12) Figure S C MR spectrum (CDCl 3, 100 Mz) of 12.
39 2 Cl C 3 5 -Methyl-6-chloro PIP (13) Figure S23. 1 MR spectrum (CDCl 3, 400 Mz) of 13.
40 Cl C 3 5 -Methyl-6-chloro PIP (13) Figure S C MR spectrum (CDCl 3, 100 Mz) of 13.
41 2 CF 3 C 3 5 -Methyl-6-trifluoromethyl PIP (14) Figure S25. 1 MR spectrum (CDCl 3, 400 Mz) of 14.
42 CF 3 C 3 5 -Methyl-6-trifluoromethyl PIP (14) Figure S C MR spectrum (CDCl 3, 100 Mz) of 14.
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