Thiazolo[5,4-d]thiazole-based covalent organic framework microspheres for blue light photocatalytic selective oxidation of amines with O2

doi:10.1016/S1872-2067(22)64127-5

Abstract

Abstract:

Covalent organic frameworks (COFs) with photoactive units have attracted significant interest in visible light photocatalysis and can present a metal-free scenario for activating O₂. As a typical photoactive unit, thiazolo[5,4-d]thiazole (TzTz) has rarely been added to COFs. However, circumventing the low reversibility of TzTz, it could be embedded into the building blocks beforehand, along with other bonds like β-ketoenamine in forming COFs. TzTz was embedded into 1,1′-biphenyl-4,4′-diamine (BD) using this approach to produce 4,4′-(TzTz-2,5-diyl)dianiline (DTz). Under organobase-modulated solvothermal conditions, combining 1,3,5-triformylphloroglucinol (Tp) with BD and DTz resulted in the production of β-ketoenamine-linked TpBD-COF and TpDTz-COF. Both TpDTz-COF and TpBD-COF are microspheres. TpDTz-COF possessed more adequate separation and charge migration than TpBD-COF. This resulted in superior performance for the blue light photocatalytic selective oxidation of benzylamine with O₂. Furthermore, with O₂ as the main oxidant, a wealth of benzylamines could be converted into imines over TpDTz-COF. Mechanistic investigations substantiate that oxidation of benzylamines obeys an electron transfer pathway, in which superoxide anion (O₂^•-) is the crucial reactive oxygen species. This study highlights the superiority of TzTz-embedded COFs in developing effective photocatalytic systems for organic transformations.

Key words: Covalent organic framework, Thiazolo[5,4-d]thiazole, Visible light, Photocatalysis, Selective oxidation

Fulin Zhang, Xia Li, Xiaoyun Dong, Huimin Hao, Xianjun Lang. Thiazolo[5,4-d]thiazole-based covalent organic framework microspheres for blue light photocatalytic selective oxidation of amines with O₂[J]. Chinese Journal of Catalysis, 2022, 43(9): 2395-2404.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(22)64127-5

https://www.cjcatal.com/EN/Y2022/V43/I9/2395

Figures/Tables 10

Fig. 1. Schematic illustration of TpDTz-COF and TpBD-COF.

Fig. 2. SEM images of TpDTz-COF (a) and TpBD-COF (b). TEM images of TpDTz-COF (c) and TpBD-COF (d).

Fig. 3. PXRD pattern of TpDTz-COF (a) and TpBD-COF (b). Nitrogen sorption isotherm of TpDTz-COF (c) and TpBD-COF (d).

Fig. 4. FTIR spectra of Tp, DTz, and TpDTz-COF (a) and Tp, BD, and TpBD-COF (b). (c) UV-vis DRS spectra of TpDTz-COF and TpBD-COF. (d) Optical bandgaps (Eg) calculated from the Kubelka-Munk formula.

Fig. 5. Mott-Schottky plots of TpDTz-COF (a) and TpBD-COF (b) at frequencies of 500, 1000, and 1500 Hz. (c) Photocurrent densities vs. time of TpDTz-COF (red) and TpBD-COF (blue). (d) EIS of TpDTz-COF (red) and TpBD-COF (blue).

Fig. 6. (a) Blue light photocatalytic oxidation of benzylamine over TpDTz-COF and TpBD-COF, reaction time: 1.7 h. (b) The influence of various light sources on the oxidation of benzylamine over TpDTz-COF. (c) Recycling stability of TpDTz-COF for the photocatalytic oxidation of benzylamine. (d) Control experiments for the selective oxidation of benzylamine over TpDTz-COF. Standard reaction conditions: COF (5 mg), CH3CN (1 mL), benzylamine (0.3 mmol), blue LEDs (460 ± 10 nm), O2 (0.1 MPa), and 1.3 h.

Table 1 Photocatalytic selective oxidation of primary amines into imines using O2 over TpDTz-COF a.

Entry	Conv.^b (%)	Sel.^b (%)
1	92	99
2	95	99
3	89	99
4	90	99
5	93	99
6	95	100
7	77	99
8	86	99
9	84	99
10	86	99
11	99	100
12	86	99

Table 2 Photocatalytic selective oxidation of secondary amines into imines with O2 over TpDTz-COF a.

Entry	Conv.^b (%)	Sel. ^b (%)
1	82	84
2	85	80
3	52	96
4	77	88
5	93	80

Fig. 7. (a) Quenching experiments to confirm the ROS for the photocatalytic selective oxidation of benzylamine with O2 over TpDTz-COF. The EPR spectra of electrons (b), O2•- (c), and 1O2 (d) generated by TpDTz-COF under blue light.

Fig. 8. A plausible mechanism for the blue light photocatalytic selective oxidation of benzylamine using O2 over TpDTz-COF.

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Thiazolo[5,4-d]thiazole-based covalent organic framework microspheres for blue light photocatalytic selective oxidation of amines with O₂

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Entry	Conv.^b (%)	Sel.^b (%)
1	92	99
2	95	99
3	89	99
4	90	99
5	93	99
6	95	100
7	77	99
8	86	99
9	84	99
10	86	99
11	99	100
12	86	99

Entry	Conv.^b (%)	Sel.^b (%)
1	92	99
2	95	99
3	89	99
4	90	99
5	93	99
6	95	100
7	77	99
8	86	99
9	84	99
10	86	99
11	99	100
12	86	99

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Entry	Conv.^b (%)	Sel.^b (%)
1	92	99
2	95	99
3	89	99
4	90	99
5	93	99
6	95	100
7	77	99
8	86	99
9	84	99
10	86	99
11	99	100
12	86	99

Entry	Conv.^b (%)	Sel.^b (%)
1	92	99
2	95	99
3	89	99
4	90	99
5	93	99
6	95	100
7	77	99
8	86	99
9	84	99
10	86	99
11	99	100
12	86	99

Entry	Conv.^b (%)	Sel.^b (%)
1	92	99
2	95	99
3	89	99
4	90	99
5	93	99
6	95	100
7	77	99
8	86	99
9	84	99
10	86	99
11	99	100
12	86	99

Entry	Conv.^b (%)	Sel.^b (%)
1	92	99
2	95	99
3	89	99
4	90	99
5	93	99
6	95	100
7	77	99
8	86	99
9	84	99
10	86	99
11	99	100
12	86	99