Fluorescence Enhancement of Unconstrained GFP Chromophore Analogues Based on the Push-Pull Substituent Effect
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1 Fluorescence Enhancement of Unconstrained GFP Chromophore Analogues Based on the Push-Pull Substituent Effect Meng-Shiue Tsai,, Chun-Lin Ou, Chi-Jui Tsai, Yen-Chin Huang, Yuan-Chung Cheng,*, Shih-Sheng Sun,*, and Jye-Shane Yang*, Department of Chemistry, National Taiwan University, Taipei 10617, Taiwan Institute of Chemistry, Academia Sinica, Taipei 11529, Taiwan and Supporting Information (62 pages) S1 Table of Contents S2 Figure S1. DFT-optimized structures of 1 4. S3 Figure S2. Solvatofluorochromic plots for 1 4. S4 Figure S3. Shape and relative energy of the frontier molecular orbitals HOMO and LUMO of 1 4. S5 Figure S4. Photographic images of fluorescence quenching induced by the electron donor trimethylamine and H-bond donors methanol and 10% water in THF for 2 4 (excited by 366 nm of a hand-help UV lamp). S6 Figure S5. Methanol titration experiments and Stern-Volmer plots for 2 4 in acetonitrile. S7 Figure S6. Triethylamine titration experiments and Stern-Volmer plots for 2 4 in acetonitrile. S8 Figure S7. Triethanolamine titration experiments and Stern-Volmer plots for 2 4 in acetonitrile. S9-S42 Figure S8-S41. 1 H- and 13 C-NMR spectra of new compounds. S43- Table S1. DFT (M06-2X/6-31+G(d))-Derived Cartesian Coordinates of S50 Ground-State Structures of 1 4. S51- Table S2. TDDFT (M06-2X/6-31+G(d))-Derived Cartesian Coordinates S62 of Excited-State Structures of 1 4. S1
2 Figure S1. DFT-optimized structures (front and side views) of (a) 1, (b) 2, (c) 3, and (d) 4 calculated at the M06-2X/6-31+G(d) level. S2
3 Figure S2. Solvatofluorochromic plots for (a) 1, (b) 2, (c) 3, and (d) 4. S3
4 Figure S3. Shape and relative energy of the frontier molecular orbitals HOMO and LUMO of 1 4. S4
5 Figure S4. Photographic images of fluorescence quenching induced by the electron donor trimethylamine and H-bond donors methanol and 10% water in THF for (a) 2, (b) 3 and (c) 4 (excited by 366 nm of a hand-help UV lamp). S5
6 Figure S5. Methanol titration experiments and Stern-Volmer plots for (a) 2, (b) 3, and (c) 4 in acetonitrile. S6
7 Figure S6. Triethylamine titration experiments and Stern-Volmer plots for (a) 2, (b) 3, and (c) 4 in acetonitrile. S7
8 Figure S7. Triethanolamine titration experiments and Stern-Volmer plots for (a) 2, (b) 3, and (c) 4 in acetonitrile. S8
9 Figure S8. 1 H (400 MHz, CDCl3) NMR spectrum of 2 at 298 K. S9
10 Figure S9. 13 C (100 MHz, CDCl3) NMR spectrum of 2 at 298 K. S10
11 Figure S10. 1 H (500 MHz, CD2Cl2) NMR spectrum of 3 at 298 K. S11
12 Figure S C (125 MHz, CD2Cl2) NMR spectrum of 3 at 298 K. S12
13 Figure S12. 1 H (500 MHz, CDCl3) NMR spectrum of 4 at 298 K. S13
14 Figure S C (125 MHz, CDCl3) NMR spectrum of 4 at 298 K. S14
15 Figure S14. 1 H (400 MHz, CDCl3) NMR spectrum of 7 at 298 K. S15
16 Figure S C (100 MHz, CDCl3) NMR spectrum of 7 at 298 K. S16
17 Figure S16. 1 H (400 MHz, CDCl3) NMR spectrum of 8 at 298 K. S17
18 Figure S C (100 MHz, CDCl3) NMR spectrum of 8 at 298 K. S18
19 Figure S18. 1 H (500 MHz, d6-dmso) NMR spectrum of 9 at 298 K. S19
20 Figure S C (125 MHz, d6-dmso) NMR spectrum of 9 at 298 K. S20
21 Figure S20. 1 H (400 MHz, d6-dmso) NMR spectrum of 10 at 298 K. S21
22 Figure S C (100 MHz, d6-dmso) NMR spectrum of 10 at 298 K. S22
23 Figure S22. 1 H (500 MHz, d6-dmso) NMR spectrum of 11 at 298 K. S23
24 Figure S C (125 MHz, d6-dmso) NMR spectrum of 11 at 298 K. S24
25 Figure S24. 1 H (500 MHz, CDCl3) NMR spectrum of 12 at 298 K. S25
26 Figure S C (125 MHz, CDCl3) NMR spectrum of 12 at 298 K. S26
27 Figure S26. 1 H (400 MHz, CDCl3) NMR spectrum of 14 at 298 K. S27
28 Figure S C (100 MHz, CDCl3) NMR spectrum of 14 at 298 K. S28
29 Figure S28. 1 H (400 MHz, CDCl3) NMR spectrum of 15 at 298 K. S29
30 Figure S C (100 MHz, CDCl3) NMR spectrum of 15 at 298 K. S30
31 Figure S30. 1 H (400 MHz, CDCl3) NMR spectrum of 16 at 298 K. S31
32 Figure S C (100 MHz, CDCl3) NMR spectrum of 16 at 298 K. S32
33 Figure S32. 1 H (500 MHz, CDCl3) NMR spectrum of 17 at 298 K. S33
34 Figure S C (125 MHz, CDCl3) NMR spectrum of 17 at 298 K. S34
35 Figure S34. 1 H (500 MHz, CDCl3) NMR spectrum of 18 at 298 K. S35
36 Figure S C (125 MHz, CDCl3) NMR spectrum of 18 at 298 K. S36
37 Figure S36. 1 H (400 MHz, CDCl3) NMR spectrum of 19 at 298 K. S37
38 Figure S C (100 MHz, CDCl3) NMR spectrum of 19 at 298 K. S38
39 Figure S38. 1 H (500 MHz, CDCl3) NMR spectrum of 20 at 298 K. S39
40 Figure S C (125 MHz, CDCl3) NMR spectrum of 20 at 298 K. S40
41 Figure S40. 1 H (500 MHz, CDCl3) NMR spectrum of 21 at 298 K. S41
42 Figure S C (125 MHz, CDCl3) NMR spectrum of 21 at 298 K. S42
43 Table S1: DFT (M06-2X/6-31+G(d))-Derived Cartesian Coordinates of Ground-State Structures 1Z C C C C C C N C C C N C C N C O C C H H H H H H H H H H H H H H H H H S43
44 1E C C C C C C N C C C N C C N C O C C H H H H H H H H H H H H H H H H H S44
45 2Z C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S45
46 2E C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S46
47 3Z C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S47
48 3E C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S48
49 4Z C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S49
50 4E C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S50
51 Table S2: TDDFT (M06-2X/6-31+G(d))-Derived Cartesian Coordinates of Excited-State Structures 1Z* C C C C C C N C C C N C C N C O C C H H H H H H H H H H H H H H H H H S51
52 1p* C C C C C C N C C C N C C N C O C C H H H H H H H H H H H H H H H H H S52
53 1E* C C C C C C N C C C N C C N C O C C H H H H H H H H H H H H H H H H H S53
54 2Z* C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S54
55 2p* C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S55
56 2E* C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S56
57 3Z* C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S57
58 3p* C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S58
59 3E* C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S59
60 4Z* C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S60
61 4p* C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S61
62 4E* C C C C C C N C C C N C C N C O C C H C H H H H H H H H H H H H H H H N S62
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