File S1 - Incorporating a Piperidinyl Group in the Fluorophore Extends the Fluorescence Lifetime of Click-Derived Cyclam-Naphthalimide Conjugates

File S1 Contains the files: Text S1. Lippert-Mataga Equation. Text S2. Synthesis of Known Compounds. Figure S1. Stokes shift () of 8 versus orientation polarizability (Δf). The red, straight line represents the best linear fit to the 13 data points [coefficient of determination R2 = 0.560, slope = (4.32±1.07)×103 cm−1, intercept = (4.41±0.26)×103 cm−1]. Figure S2. Stokes shift () of 9 versus orientation polarizability (Δf). The red, straight line represents the best linear fit to the 13 data points [coefficient of determination R2 = 0.392, slope = (3.00±1.02)×103 cm−1, intercept = (4.61±0.25)×103 cm−1]. Figure S3. Stokes shift () of 10 versus orientation polarizability (Δf). The red, straight line represents the best linear fit to the 13 data points [coefficient of determination R2 = 0.562, slope = (4.07±1.00)×103 cm−1, intercept = (4.53±0.25)×103 cm−1]. Figure S4. Fluorescence spectra of 8 (10 µM) in the presence of various metal ions. Experiments were carried out in HEPES buffer (10 mM, pH 7.4) at 25°C and the fluorescence emission spectra were recorded about 5 min after addition of various metal ions (1 equiv.). Figure S5. Fluorescence spectra of 9 (10 µM) in the presence of various metal ions. Experiments were carried out in HEPES buffer (10 mM, pH 7.4) at 25°C and the fluorescence emission spectra were recorded about 5 min after addition of various metal ions (1 equiv.). Figure S6. Fluorescence spectra of 10 (10 µM) in the presence of various metal ions. Experiments were carried out in HEPES buffer (10 mM, pH 7.4) at 25°C and the fluorescence emission spectra were recorded about 5 min after addition of various metal ions (1 equiv.). Figure S7. UV-Vis spectra of 8 (10 µM) in the presence of various metal ions. Experiments were carried out in HEPES buffer (10 mM, pH 7.4) at 25°C and the UV-Vis spectra were recorded about 5 min after addition of various metal ions (1 equiv.). Figure S8. UV-Vis spectra of 9 (10 µM) in the presence of various metal ions. Experiments were carried out in HEPES buffer (10 mM, pH 7.4) at 25°C and the UV-Vis spectra were recorded about 5 min after addition of various metal ions (1 equiv.). Figure S9. UV-Vis spectra of 10 (10 µM) in the presence of various metal ions. Experiments were carried out in HEPES buffer (10 mM, pH 7.4) at 25°C and the UV-Vis spectra were recorded about 5 min after addition of various metal ions (1 equiv.). Figure S10. Fluorescence emission of 8 (10 µM) in the absence and presence of Cu2+ (1 equiv.) over a range of pH values. Experiments were carried out in HEPES buffer (10 mM, pH 7.4) at 25°C. Figure S11. Fluorescence emission of 9 (10 µM) in the absence and presence of Cu2+ (1 equiv.) over a range of pH values. Experiments were carried out in HEPES buffer (10 mM, pH 7.4) at 25°C. Figure S12. Fluorescence emission of 10 (10 µM) in the absence and presence of Cu2+ (1 equiv.) over a range of pH values. Experiments were carried out in HEPES buffer (10 mM, pH 7.4) at 25°C. Figure S13. Synthesis of 2-azidoethyl-tri-Boc cyclam S3. Reagents and conditions: (a) (i) NaN3, H2O, reflux, o/n; (ii) p-toluenesulfonyl chloride, Et3N, rt, 6 h; (iii) glycine, rt, 2 h, 65%; (b) tri-Boc cyclam, Na2CO3, CH3CN, reflux, 96 h, 66%. Figure S14. Synthesis of compound 12. Reagents and conditions: (a) piperidine, 2-methoxyethanol, reflux, 36 h, 86%; (b) 4-bromoaniline, piperidine, 2-methoxyethanol, reflux, 72 h, 90%. Figure S15. Synthesis of compound 17. Reagents and conditions: (a) 2-aminoethanol, EtOH, reflux, 22 h, 92%; (b) PBr3, pyridine, THF, 50°C, 16 h, 60%; (c) NaN3, EtOH, reflux, 6 h, 80%. Figure S16. 1H NMR spectrum (300 MHz) of 13 in CDCl3. Figure S17. 13C NMR spectrum (75 MHz) of 13 in CDCl3. Figure S18. 1H NMR spectrum (300 MHz) of 14 in CDCl3. Figure S19. 13C NMR spectrum (75 MHz) of 14 in CDCl3. Figure S20. 1H NMR spectrum (400 MHz) of 8 in CDCl3. Figure S21. 13C NMR spectrum (100 MHz) of 8 in CDCl3. Figure S22. 1H NMR spectrum (400 MHz) of 18 in CDCl3. Figure S23. 13C NMR spectrum (100 MHz) of 18 in CDCl3. Figure S24. 1H NMR spectrum (400 MHz) of 9 in CDCl3. Figure S25. 13C NMR spectrum (100 MHz) of 9 in CDCl3. Figure S26. 1H NMR spectrum (300 MHz) of 19 in CDCl3. Figure S27. 13C NMR spectrum (75 MHz) of 19 in CDCl3. Figure S28. 1H NMR spectrum (400 MHz) of 20 in CDCl3. Figure S29. 13C NMR spectrum (75 MHz) of 20 in CDCl3. Figure S30. 1H NMR spectrum (300 MHz) of 21 in CDCl3. Figure S31. 13C NMR spectrum (75 MHz) of 21 in CDCl3. Figure S32. 1H NMR spectrum (400 MHz) of 10 in CDCl3. Figure S33. 13C NMR spectrum (100 MHz) of 10 in CDCl3. (ZIP)