Citation: Shi Li, Wenshuai Zhao, Yong Qi, Wenbin Niu, Wei Ma, Bingtao Tang, Shufen Zhang. Hydrogen bonding induced ultra-highly thermal stability of azo dyes for color films[J]. Chinese Chemical Letters, ;2025, 36(9): 110653. doi: 10.1016/j.cclet.2024.110653 shu

Hydrogen bonding induced ultra-highly thermal stability of azo dyes for color films

State Key Laboratory of Fine Chemicals, Frontier Science Center for Smart Materials, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, China

zhangshf@dlut.edu.cn

Received Date: 5 September 2024
Revised Date: 11 November 2024
Accepted Date: 19 November 2024
Available Online: 20 November 2024

Figures(4)

Dye-based color films are increasingly considered as viable alternatives to pigment-based color films in complementary metal-oxide-semiconductor (CMOS) image sensors. Herein, a series of azo dyes utilizing 5-methyl-2-phenyl-4-(2-phenylhydrazono)-2,4-dihydro-3H-pyrazol-3-one as the coupling component and aromatic amines with various electron-withdrawing groups (NO₂, CN, Br) as diazo components were designed and synthesized. The presence of intermolecular hydrogen bonding between the hydrogen atom on the NH group and the oxygen atom of the C=O group of the hydrazo structure facilitates the formation of a stable six-membered ring. Additionally, the electron-withdrawing groups in the diazo component further stabilize this hydrogen-bonded structure. As a result, these azo dyes (P-2, P-3, P-4, P-5) exhibit not only excellent light stability but also ultra-highly thermal stability (T_d > 260 ℃). Therein, the synthesized dyes P-2 and P-3 with great bright yellow color (~400 nm), proper solubility (~6.00 g/100 g) were selected to make for color films. And their dye-based color films displayed ultra-highly thermal and light stability (color difference ΔE < 3). Notably, the increased planarity of the molecular structure by hydrogen bonding for the novel dyes ensures a balance between high transmittance (>90%) in the 550–780 nm wavelength range and the solvent resistance of the dye-based color films. This work contributes to the advancement of next-generation smart CMOS devices and offers valuable insights into the design of azo dyes for applications in the field of organic electronics.
- Visual identification,
- Azo dyes,
- Color films,
- Thermal stability,
- Hydrogen bonding
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