期刊
CHEMPHOTOCHEM
卷 4, 期 7, 页码 481-486出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cptc.201900279
关键词
aggregation-induced emission; amino acids; amphiphiles; self-assembly; supramolecular chemistry
资金
- Ministry of Science and Technology of the Republic of China, Taiwan [MOST 108-2113-M-033-008-, MOST 107-2113-M-033-006-, MOST 107-2633-M-033-001-]
Although fluorescent materials based on diphenylamine (DPA) conjugated with cyanostilbene (CS) have been developed for biological applications as aggregation-induced emission chromophores with long-wavelength emissions, only DPACS derivatives of very high polarity and low polarity have been investigated previously. Herein, we report three DPACS-capped amino acid amphiphiles - DPACS-G, DPACS-S, and DPACS-D - of various hydrophobicities. Their self-assembly and photophysical properties in aqueous media are dependent upon the nature of their amino acid residues. Interestingly, under alkaline conditions, the introduction of a serine (S) residue in the DPACS chromophore (i. e., DPACS-S) resulted in a self-assembled hydrogel and the formation of nanorods with aggregation-induced emission enhancement characteristics. Experimental and theoretical studies of DPACS-S revealed that pi-pi stacking, electrostatic interactions, and extended intermolecular hydrogen bonding were the main driving forces behind its self-assembly.
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