TY - JOUR
T1 - Helical Sulfono-γ-AApeptides with Aggregation-Induced Emission and Circularly Polarized Luminescence
AU - Shi, Yan
AU - Yin, Guangqiang
AU - Yan, Zhiping
AU - Sang, Peng
AU - Wang, Minghui
AU - Brzozowski, Robert
AU - Eswara, Prahathees
AU - Wojtas, Lukasz
AU - Zheng, Youxuan
AU - Li, Xiaopeng
AU - Cai, Jianfeng
N1 - Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/8/14
Y1 - 2019/8/14
N2 - Aggregation-induced emission (AIE) was intensively studied because of packing of small molecules and polymers; however, mid-molecular-weight (1000-3000) molecular scaffold containing a precise number of AIE luminogens is rare. Herein, we report the investigation of three tetraphenylethylene (TPE)-modified sulfono-γ-AApeptides in which multiple TPE moieties are conjugated to the chiral right-handed helical peptidomimetic backbone as functional side chains. The crystal structure of the TPE-α/sulfono-γ-AA peptide 1 demonstrates that because of the rigid helical scaffold of the TPE-α/sulfono-γ-AA peptides, the intramolecular rotations of the TPE with short linker are restricted, therefore leading to the boosted fluorescent emission in solution. Peptides 2 and 3 exhibit aggregation-induced emission enhancement (AIEE), possibly because of the combination of both AIE and rotation restriction. Moreover, because of their preoriented assembly induced by the right-handed helical scaffold, these emissive chiral luminogens show effective circularly polarized luminescence signals with high dissymmetry factor glum. Finally, the amphiphilic nature of TPE-α/sulfono-γ-AA peptides could enable them to penetrate the bacterial membranes and exhibit strong fluorescence. Their antimicrobial activity and labeling-free character could further augment their potential applications in both materials and biomedical sciences.
AB - Aggregation-induced emission (AIE) was intensively studied because of packing of small molecules and polymers; however, mid-molecular-weight (1000-3000) molecular scaffold containing a precise number of AIE luminogens is rare. Herein, we report the investigation of three tetraphenylethylene (TPE)-modified sulfono-γ-AApeptides in which multiple TPE moieties are conjugated to the chiral right-handed helical peptidomimetic backbone as functional side chains. The crystal structure of the TPE-α/sulfono-γ-AA peptide 1 demonstrates that because of the rigid helical scaffold of the TPE-α/sulfono-γ-AA peptides, the intramolecular rotations of the TPE with short linker are restricted, therefore leading to the boosted fluorescent emission in solution. Peptides 2 and 3 exhibit aggregation-induced emission enhancement (AIEE), possibly because of the combination of both AIE and rotation restriction. Moreover, because of their preoriented assembly induced by the right-handed helical scaffold, these emissive chiral luminogens show effective circularly polarized luminescence signals with high dissymmetry factor glum. Finally, the amphiphilic nature of TPE-α/sulfono-γ-AA peptides could enable them to penetrate the bacterial membranes and exhibit strong fluorescence. Their antimicrobial activity and labeling-free character could further augment their potential applications in both materials and biomedical sciences.
UR - http://www.scopus.com/inward/record.url?scp=85070981908&partnerID=8YFLogxK
U2 - 10.1021/jacs.9b05329
DO - 10.1021/jacs.9b05329
M3 - Article
C2 - 31335135
AN - SCOPUS:85070981908
SN - 0002-7863
VL - 141
SP - 12697
EP - 12706
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 32
ER -