Abstract
Luminol is considered as an efficient sycpstem in electrochemiluminescence (ECL) measurements for the detection of hydrogen peroxide. In this paper, new luminol imide derivatives with different alkyl substituent chains were designed and synthesized. Their gelation behaviors in 26 solvents were tested as novel low molecular mass organic gelators. It was shown that the length and number of alkyl substituent chains linked to a benzene ring in gelators played a crucial role in the gelation behavior of all compounds in various organic solvents. Longer alkyl chains in molecular skeletons in present gelators are favorable for the gelation of organic solvents. Scanning electron microscope and atomic force microscope observations revealed that the gelator molecules self-assemble into different micro/nanoscale aggregates from a dot, flower, belt, rod, and lamella to wrinkle with change of solvents. Spectral studies indicated that there existed different H-bond formations and hydrophobic forces, depending on the alkyl substituent chains in molecular skeletons. The present work may give some insight to the design and characteristic of new versatile soft materials and potential ECL biosensors with special molecular structures.
Highlights
The self-assembly of small functional molecules into supramolecular structures is a powerful approach toward the development of new nanoscale materials and devices [1,2,3,4,5,6,7]
It seemed that longer alkyl chains in molecular skeletons in present gelators are favorable for the intermolecular stacking and subsequent gelation of organic solvents, which was similar to the previous relative reports [36,37]
The reasons for the strengthening of the gelation behaviors for TC18-Lu and TC16-Lu can be assigned to the change of hydrophobic force and the spatial conformation of the gelators due to longer alkyl substituent chains in molecular skeletons, which may increase the ability of the gelator molecules to self-assemble into ordered structures, a necessity for forming organized network structures
Summary
The self-assembly of small functional molecules into supramolecular structures is a powerful approach toward the development of new nanoscale materials and devices [1,2,3,4,5,6,7]. We reported the design and synthesis of functional luminol derivatives with different substituted groups and investigated the interfacial assembly of these compounds with different methods [28,29]. Therein, their potential for ECL measurement has been demonstrated first. In our reported work, the gelation properties of some cholesterol imide derivatives consisting of cholesteryl units and photoresponsive azobenzene substituent groups have been investigated [31]. Therein, we have investigated the spacer effect on the microstructures of such organogels and found that various kinds of hydrogen bond interactions among the molecules play an important role in the formation of gels
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