Rapid room-temperature phosphorescence chiral recognition of natural amino acids

• Published in: Nature communications Vol. 15; no. 1; p. 3314
• Main Authors: Chen, Xiaoyu, Zhu, Renlong, Zhang, Baicheng, Zhang, Xiaolong, Cheng, Aoyuan, Liu, Hongping, Gao, Ruiying, Zhang, Xuepeng, Chen, Biao, Ye, Shuji, Jiang, Jun, Zhang, Guoqing
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 17.04.2024; Nature Publishing Group; Nature Portfolio
• Subjects: 639/638/11/511; 639/638/298/398; 639/638/439; 639/638/440/527/1819; Afterglows; Amino acids; Amino Acids - chemistry; Analytical chemistry; Benzamide; Complementarity; Energy transfer; Evaporation; Handedness; Humanities and Social Sciences; Luminescence; Molecular Structure; multidisciplinary; Phenylalanine; Phosphorescence; Recognition; Room temperature; Science; Science (multidisciplinary); Temperature; Tetrahydrofuran
• ISSN: 2041-1723; 2041-1723
• DOI: 10.1038/s41467-024-47648-z

Chiral recognition of amino acids is very important in both chemical and life sciences. Although chiral recognition with luminescence has many advantages such as being inexpensive, it is usually slow and lacks generality as the recognition module relies on structural complementarity. Here, we show that one single molecular-solid sensor, L-phenylalanine derived benzamide, can manifest the structural difference between the natural, left-handed amino acid and its right-handed counterpart via the difference of room-temperature phosphorescence (RTP) irrespective of the specific chemical structure. To realize rapid and reliable sensing, the doped samples are obtained as nanocrystals from evaporation of the tetrahydrofuran solutions, which allows for efficient triplet-triplet energy transfer to the chiral analytes generated in situ from chiral amino acids. The results show that L-analytes induce strong RTP, whereas the unnatural D-analytes produce barely any afterglow. The method expands the scope of luminescence chiral sensing by lessening the requirement for specific molecular structures. Chiral recognition of amino acids with luminescence, despite its advantages, is usually slow and lacks generality. Here, the authors demonstrate that L-phenylalanine derived benzamide can manifest the structural difference between the natural, left-handed amino acid and its right-handed counterpart via the difference in room-temperature phosphorescence, irrespective of the specific chemical structure.