Synthesis and aggregation properties of boron-dipyrromethene dyes conjugated with guanine units

Synthesis and aggregation properties of boron-dipyrromethene dyes conjugated with guanine units
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鸟嘌呤单元共轭硼二吡咯亚甲基染料的合成及聚集性能

DOI:
10.1142/s108842461850089x
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发表时间:
2018-08
影响因子:
1.5
通讯作者:
Chen Zhijian
Chen Zhijian
中科院分区:
化学4区
文献类型:
--
作者:
Li Fen;Zhang Yongjie;Zhou Lina;Zhang Xin;Chen Zhijian

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合成了两种含共轭鸟嘌呤基团(G-BODIPY)1和2的B-二吡咯亚甲基染料,并对它们进行了表征。用X-射线结晶学、核磁共振氢谱和紫外可见光谱研究了这些染料的自组装性能。X-射线晶体结构研究表明,由于分子间氢键和[分子式:见文本]-[分子式:见文本]堆积作用,G-BODIPY 1自组装成带状结构。依赖于浓度的[公式:见文本]H核磁共振实验证实了染料1和2在溶液中形成了鸟嘌呤单元的氢键。在K[公式:见文本]的存在下,在[公式:见文本]H核磁共振研究中观察到了形成环状G-四链体结构的特征信号。通过改变溶剂的极性和温度,用紫外-可见吸收光谱进一步研究了G-BODIPY染料的聚集情况。得到了染料1的H型聚集体,其特征是一个新的亚色移位的吸收带[公式:见文本]461 nm。在K[式:见正文]的存在下,观察到染料1的H-聚集体的稳定性增强。
Two boron-dipyrromethene dyes bearing a conjugated guanine unit (G-BODIPYs) 1 and 2 were synthesized and fully characterized. The self-assembly properties of these dyes were investigated by X-ray crystallography, [Formula: see text]H NMR and UV-vis spectroscopy. As revealed by X-ray crystal structure studies, G-BODIPY 1 self-assembled into ribbon-like structures due to the intermolecular hydrogen bonding and [Formula: see text]–[Formula: see text] stacking interaction. Concentration-dependent [Formula: see text]H NMR experiments confirmed the formation of hydrogen bonds of the guanine units in solution for both dye 1 and 2. In the presence of K[Formula: see text], the characteristic signals for the formation of cyclic G-quadruplex structures were observed in the [Formula: see text]H NMR study. Aggregation of G-BODIPY dyes was further monitored by UV-vis absorption spectroscopy by varying the solvent polarity and temperature. H-type aggregates of dye 1, which was characterized by a new hypsochromically shifted absorption band with [Formula: see text] 461 nm, was obtained. In the presence of K[Formula: see text], the enhancement of stability was observed for the H-aggregates of dye 1.
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影响因子: 15
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