# Decoration of Polyfluorene-Wrapped Carbon Nanotubes with Photoleavable Side-Chains
## 3 Materials and Methods
### Experimental Procedures
#### 3.2.5 (5-(2-(2-(2-(2-methoxyethoxy)ethoxy)-2-nitrophenyl)methanol (6) [89]  
A 20 mL vial equipped with a stir bar was charged with compound 5 (0.75 g, 2.24 mmol) in 6 mL of dry THF. Sodium borohydride (0.13 g, 3.35 mmol) was added, and the solution was stirred at 0 \({}^{\circ}\)C for 1 h. After completion, the mixture was diluted with EtOAc, filtered through a silica plug using EtOAc as eluent, and concentrated in vacuo to give a yellowish solid (0.64 g, 85%). \({}^{1}\)H-NMR (600 MHz, CDCl\({}_{3}\)): 8.17 (d, \(J\) = 9.04 Hz, 1H), 7.30 (d, \(J\) = 2.9 Hz, 1H), 6.90 (dd, \(J\) = 9.05, \(J\) = 2.9 Hz, 1H), 4.98 (s, 2H), 4.47 (m, 2H), 3.89 (m, 2H), 3.73 (m, 2H), 3.67 (m, 2H), 3.64 (m, 2H), 3.54 (m, 2H), 3.37 (s,3H). 3.2.6. 4-(2-(2-(2-(2-methoxyethoxy)ethoxy)-1-nitro-2-((prop-2-yn-1-yloxy)methyl) -benzene (oNB-TEG-alkyne)  
A 100 mL round bottom flask equipped with a stir bar was charged with compound 6 (0.6 mg, 1.90 mmol) and sodium hydride (54 mg, 2.28 mmol) in 20 mL of dry THF. The solution was stirred at 0 \({}^{\circ}\)C for 1 h, and propargyl bromide (0.34 g, 2.85 mmol) was added dropwise. The mixture was stirred overnight at RT, then quenched with water (10 mL), extracted with dichloromethane (3 \(\times\) 20 mL), washed with water (3 \(\times\) 30 mL) and brine (3 \(\times\) 30 mL). The organic layer was dried with MgSO\({}_{4}\), and concentrated in vacuo. The compound was purified by flash chromatography Hex/EtOAc (0% to 90%) to give a brown oil (0.5 g, 75%). \({}^{1}\)H-NMR (600 MHz; CDCl\({}_{3}\)): 8.16 (d, \(J\) = 9.1 Hz, 1H), 7.30 (d, \(J\) = 2.8 Hz, 1H), 6.91 (dd, \(J\) = 9.1, 2.8 Hz, 1H), 4.99 (d, \(J\) = 6.5 Hz, 2H), 4.27-4.25 (m, 2H), 3.90-3.88 (m, 2H), 3.74-3.63 (m, 6H), 3.55-3.54 (m, 2H), 3.37 (s, 3H), 2.71 (t, \(J\) = 6.6 Hz, 1H). \({}^{13}\)C-NMR (151 MHz; CDCl3): 6 163.5, 140.49, 140.34, 127.9, 114.6, 113.9, 71.9, 70.89, 70.70, 70.55, 69.6, 68.2, 62.9, 59.0. ESI-MS: \(m/z\) calculated for C\({}_{17}\)H\({}_{23}\)NO\({}_{7}\) [M\({}^{+}\)]: 353.15 found [M+Na]\({}^{+}\): 376.1. 3.2.7. Triethylene glycol methyl propargyl ether (TEG-alkyne) [90]  
A round bottom flask equipped with a stir bar was charged with triethylene glycol monomethyl ether (1.00 g, 6.09 mmol) in 60 mL of anhydrous THF at 0 \({}^{\circ}\)C. NaH (0.28 g, 6.69 mmol) was added to the solution, and the reaction mixture was stirred at 0 \({}^{\circ}\)C. After 1 h, propargyl bromide (80% in toluene, 1.43 g, 7.91 mmol) was added dropwise. The reaction mixture was stirred at RT overnight, quenched with water (30 mL) and extracted with DCM (3 \(\times\) 30 mL). The organic layers were combined, washed with brine (3 \(\times\) 25 mL), dried with MgSO\({}_{4}\) and concentrated in vacuo to afford TEG-alkyne as an orange oil (1.05 g, 85%). \({}^{1}\)H-NMR (600 MHz; CDCl\({}_{3}\)): 8 4.20 (d, \(J\) = 2.4 Hz, 2H), 3.71-3.63 (m, 10H), 3.55-3.54 (m, 2H), 3.37 (s, 3H), 2.42 (t, phJ = 2.4 Hz, 1H). 3.2.8. CuAAC Procedure for PF-TEG (P1)  
A glass vial was charged with PF-N\({}_{3}\) (30 mg, 70 \(\upmu\)mol) in 7 mL THF and 2.1 equivalents of TEG-alkyne (30 mg, 150 \(\upmu\)mol). To the reaction mixture, 4 mg of Cu(OAc) and 10 equivalents of Hunig's base with respect to Cu(OAc) (40 mg, 0.36 mmol) were added. The reaction mixture was stirred at RT, and reaction progress was monitored by IR spectroscopy for the disappearance of the azide stretch at \(\sim\)2090 cm\({}^{-1}\). The solution was filtered through an alumina plug, concentrated in vacuo and redissolved in a minimum of THF. The polymer was precipitated in \(\sim\)50 mL of cold MeOH to give a yellow solid (51 mg, 87%). \({}^{1}\)H-NMR (600 MHz; CDCl\({}_{3}\)): 8 7.90-7.85 (m, 2H), 7.77-7.67 (m, 4H), 7.53-7.48 (m, 2H), 4.69-4.63 (m, 4H), 4.27-4.19 (m, 4H), 3.69-3.64 (m, 18H), 3.58-3.52 (m, 4H), 3.39-3.37 (m, 6H), 2.20-2.09 (m, 4H), 1.79-1.71 (m, 4H), 1.23-1.11 (m, 10H), 0.88-0.77 (m, 4H). 3.2.9. CuAAC Procedure for PF-oNB-TEG (P2)  
A glass vial was charged with PF-N\({}_{3}\) (30 mg, 70 \(\upmu\)mol) in 7 mL THF and 2.1 equivalents of \(\upmu\)NB-TEG-alkyne (50 mg, 150 \(\upmu\)mol).