TY - JOUR
T1 - Aggregation-Induced Emissive and Circularly Polarized Homogeneous Sulfono-γ-AApeptide Foldamers
AU - Shi, Yan
AU - Sang, Peng
AU - Yin, Guangqiang
AU - Gao, Ruixuan
AU - Liang, Xiao
AU - Brzozowski, Robert
AU - Odom, Timothy
AU - Eswara, Prahathees
AU - Zheng, Youxuan
AU - Li, Xiaopeng
AU - Cai, Jianfeng
N1 - Publisher Copyright:
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2020/7/1
Y1 - 2020/7/1
N2 - Through continuous efforts in developing a new class of foldamers, homogeneous sulfono-γ-AApeptides have been designed and synthesized using tetraphenylethylene (TPE) moieties attached to the backbone as luminogenic sidechains. Based on previous crystal structures, it is found that these foldamers adopted a left-handed 414-helix. Due to the constraint of the helical scaffold, the rotation of the TPE moieties is restricted, leading to fluorescent emissive properties with high quantum yields not only at the aggregate state but also in solution. Investigation of the relationship between the structure and fluorescence behavior reveals that emission is induced by the combined effect of the aggregation-induced emission and the rotated restriction from the backbone. Furthermore, as the packing mode of the luminogens can be precisely adjusted by the helical backbone, these foldamers are found to be circularly polarizable with relatively large luminescence dissymmetry factor. Interestingly, possessing cationic amphipathic structures similar to that of host-defense peptides, these sulfono-γ-AApeptides are able to inhibit the growth of Gram-positive bacteria, methicillin-resistant Staphylococcus aureus through membrane interactions.
AB - Through continuous efforts in developing a new class of foldamers, homogeneous sulfono-γ-AApeptides have been designed and synthesized using tetraphenylethylene (TPE) moieties attached to the backbone as luminogenic sidechains. Based on previous crystal structures, it is found that these foldamers adopted a left-handed 414-helix. Due to the constraint of the helical scaffold, the rotation of the TPE moieties is restricted, leading to fluorescent emissive properties with high quantum yields not only at the aggregate state but also in solution. Investigation of the relationship between the structure and fluorescence behavior reveals that emission is induced by the combined effect of the aggregation-induced emission and the rotated restriction from the backbone. Furthermore, as the packing mode of the luminogens can be precisely adjusted by the helical backbone, these foldamers are found to be circularly polarizable with relatively large luminescence dissymmetry factor. Interestingly, possessing cationic amphipathic structures similar to that of host-defense peptides, these sulfono-γ-AApeptides are able to inhibit the growth of Gram-positive bacteria, methicillin-resistant Staphylococcus aureus through membrane interactions.
KW - aggregation-induced emission
KW - antibacterial
KW - circularly-polarized luminescence
KW - helical conformation
KW - peptides
UR - http://www.scopus.com/inward/record.url?scp=85083739760&partnerID=8YFLogxK
U2 - 10.1002/adom.201902122
DO - 10.1002/adom.201902122
M3 - Article
AN - SCOPUS:85083739760
SN - 2195-1071
VL - 8
JO - Advanced Optical Materials
JF - Advanced Optical Materials
IS - 14
M1 - 1902122
ER -