A covalent organic framework material with a spiropyran molecular switch and its preparation method and application
A covalent organic framework and molecular switch technology, applied in the direction of organic chemistry, etc., can solve the problems of low open-loop and closed-loop conversion rate, low number of repeated use, poor fatigue resistance, etc., and achieve excellent fatigue resistance and high open-closed loop conversion. efficiency, good thermal stability
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Embodiment 1
[0056] The synthesis of azide spiropyran comprises the following steps:
[0057] (1) Synthesis of 1-(2-hydroxyethyl)-2,3,3-trimethyl-3H-indole-1-ammonium bromide.
[0058] In a dry round bottom flask was added 2,3,3-trimethylindole 1 (5.0 g, 31 mmol) and 50 mL of toluene. After adding 2-bromoethanol (4.7 g, 38 mmol), the reaction mixture was heated to 110° C. and stirred for 12 h. After cooling to room temperature, the precipitated material was isolated by vacuum filtration and washed with cold toluene and then diethyl ether to give the product 1-(2-hydroxyethyl)-2,3,3-trimethyl as a pale pink salt -3H-Indole-1-ammonium bromide (8.7 g, 30 mmol, 97%). 1 H-NMR (400MHz, DMSO-d6) δ = 7.98 (dd, J = 5.6, 3.4Hz, 1H, H7), 7.85 (dd, J = 5.8, 2.9Hz, 1H, H4), 7.63–7.55 (m, 2H,H5,H6),4.64–4.58(t,J=5.1Hz,2H,HA),3.90–3.84(t,J=5.1Hz,2H,HB),2.83(s,3H,C2-Me), 1.55 (s, 6H, C3-Me2). 13 C-NMR (101 MHz, DMSO-d6) δ=197.73, 141.80, 141.14, 129.27, 128.78, 123.45, 115.61, 57.74, 54.24, 50.31, 22...
Embodiment 2
[0073] The synthesis of BPNA-COF comprises the following steps:
[0074] Into a 10 mL Pyrex glass tube was charged 1,3,5-tris(4-aminophenyl)benzene (TPBA) (28.1 mg, 0.08 mmol), 2,6-bis(2-propynyloxy)naphthalene-1 , 5-Dicarbaldehyde (35.5 mg, 0.12 mmol) and 1 mL of ethanol. The resulting suspension was sonicated at room temperature for 30 s, and then 200 μL of 6 M acetic acid was added. Perform degassing treatment, freeze-thaw three cycles, seal and heat at 120°C for 3 days. The resulting yellow powder was collected by filtration, washed with THF (3×20 mL), and then dried in vacuo at 120° C. for 24 h to give BPNA-COF (34 mg) as a yellow powder in 71% isolated yield.
[0075] The reaction process is as follows:
[0076]
Embodiment 3
[0078] The synthesis of covalent organic framework material (BPNA-COF-SPY(SP)) with spiropyran photomolecular switch includes the following steps:
[0079] In a 10 mL Pyrex tube, azidospiropyran (98 mg), cuprous iodide (2.4 mg), BPNA-COF (48 mg) and anhydrous dried N,N-dimethylformamide (1 mL) were added. The tubes were degassed and sealed by three freeze-thaw cycles, then 80 μL of triethylamine was added, and the mixture was reacted at room temperature for 72 hours. The precipitate was collected by centrifugation, washed five times with THF and acetone, and dried under vacuum at room temperature to give an orange powder BPNA-COF-SPY (78 mg) in isolated yield.
[0080] The reaction process is as follows:
[0081]
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