Helical Sulfono-γ-AApeptides with Aggregation-Induced Emission and Circularly Polarized Luminescence.
Helical Sulfono-γ-AApeptides with Aggregation-Induced Emission and Circularly Polarized Luminescence.
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DOI：
10.1021/jacs.9b05329
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发表时间：
2019-08-14
影响因子：
15
通讯作者：
Cai, Jianfeng
中科院分区：
文献类型：
--
作者：
Shi, Yan;Yin, Guangqiang;Yan, Zhiping;Sang, Peng;Wang, Minghui;Brzozowski, Robert;Eswara, Prahathees;Wojtas, Lukasz;Zheng, Youxuan;Li, Xiaopeng;Cai, Jianfeng
聚集诱导发光（AIE）由于小分子和聚合物的堆积而被广泛研究;然而，包含精确数量的AIE发光团的中分子量（1000 - 3000）分子支架是罕见的。在此，我们报告了三个四苯乙烯（TPE）修饰的磺酰基-γ-AA肽的研究，其中多个TPE部分作为功能性侧链缀合到手性右手螺旋肽模拟物骨架上。TPE-α/磺基-γ-AA肽1的晶体结构表明，由于TPE-α/磺基-γ-AA肽的刚性螺旋支架，具有短接头的TPE的分子内旋转受到限制，因此导致溶液中增强的荧光发射。肽2和3表现出聚集诱导的发射增强（AIEE），可能是因为AIE和旋转限制的组合。此外，由于它们的预取向组装诱导的右手螺旋支架，这些发射手性发光体显示出有效的圆偏振发光信号与高不对称因子glum。最后，TPE-α/磺基-γ-AA肽的两亲性使它们能够穿透细菌膜并显示出强荧光。它们的抗微生物活性和免标记特性可以进一步增加它们在材料和生物医学科学中的潜在应用。
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.
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