A Pillar[5]arene-Based π-Conjugated Dye Used for Fluorescence Sensing of L-Arginine

doi:10.6023/cjoc202411015

Abstract

In the past decade, people have conducted extensive research on the synthesis and application properties of various functionalized pillararenes. Pillararenes show good application prospects in the field of sensors due to the rich host-guest recognition in their rigid electron-rich cavities. However, most reported pillararenes are functionalized by alkoxy modification, which results in poor charge transfer nature and weak fluorescence response. A π-conjugated charge-transfer system P5BN was obtained by introducing electron-donating triarylamine (Ar₃N) and electron-deficient triarylborane (Ar₃B) into pillar[5]arene skeleton, which significantly improved its luminescence behavior and was further used for fluorescence detection applications. The molecular structure showed that P5BN provided a good macrocyclic cavity to encapsulate amino acids molecules of suitable size. It was found that P5BN, as a fluorescent sensor, showed a highly sensitive and selective response to L-arginine (L-Arg), resulting in a significant enhancement of the fluorescence at 408 nm of P5BN with the lowest detection concentration being 2.21×10^－8 mol/L. The recognition mechanism was demonstrated through experiments and DFT theoretical calculations.

Key words: fluorescent sensor, host-guest recognition, pillar[5]arene, L-arginine, density functional theory (DFT) calculations

Cite this article

Xiaopeng Ling, Shaoping Tao, Qi Lin, Bingbing Shi, Hong Yao, Taibao Wei, Jinfa Chen. A Pillar[5]arene-Based π-Conjugated Dye Used for Fluorescence Sensing of L-Arginine[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2480-2485.

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Fig. & Tab. 5

Scheme 1. Research foundation and design strategy of pillar[5]arene-based π-conjugated emitter P5BN with enhanced luminescence and host-guest recognition

Figure 1. Fluorescence responses P5BN (c=2.0×10－6 mol/L, λex=345 nm) to various solutions of amino acids (4.0×10－6 mol/L) in DMSO solution Inset: photographs of solutions before and after the addition of L-Arg under 365 nm UV irradiation

Figure 2. Fluorescence intensity of P5BN (c=2.0×10－6 mol/L, λex=345 nm) at 408 nm with addition of L-Arg (4.0×10－6 mol/L) in the presence of competition ions (4.0×10－6 mol/L) in DMSO solution

Figure 3. Fluorescence changes of P5BN (c=2.0×10－6 mol/L, λex=345 nm) in the presence of different equiv. of L-Arg in DMSO solution

Figure 4. (a) Calculated electrostatic potentials (ESP) mapped onto the electron density isosurfaces in P5BN, L-Arg and P5BN@L-Arg; (b) Independent Gradient Model based on Hirsh- feld partition (IGMH) diagram of P5BN@L-Arg at the B3LYP/6- 31G(d,p) level

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