Formation and regulation of supramolecular chirality in organogel via addition of tartaric acid

Abstract

A new 1,8-naphthalimide derivative was prepared in which the C-4 position was substituted by pyridin-4-ol. This derivative shows good gelation property that can gelate most of polar solvents. As an achiral molecule, helical fibre morphology was observed when the compound gelated acetone solvent. When 0.5 eq of D-tartaric acid or L-tartaric acid was added to the gel, the helical morphology was changed from left-handed to right-handed structure. This result was further proved by circular dichroism measurement. FT-IR experiment showed the formation of intermolecular H-bond between the gelator and tartaric acid. The photophysical properties of gelator had no difference before and after addition of tartaric acid; whereas the lamellar structure was varied by addition of tartaric acid.

Functional π-Gelators and Their Applications

“…Hence the developments until August 2013 are accounted in this section. It includes articles related to general aspects of gelation, − different type of gelators, − azobenzene − (section 2.1), stilbene − (section 2.2), dithienylethenes − (section 2.4), diacetylenes − (section 2.7), miscellaneous photoresponsive chromophores , (section 2.9), naphthalimides − (section 3.2), PBI − (section 3.3), squaraines − (section 3.7), coumarins − (section 3.9), dye doped gels<...…”

Synthesis, Structure, and Topological Studies of Solvates and Salts of a Chiral Zwitterionic Host N-(2-Imidazol-5-yl-1-carboxyethyl)-1,8-naphthalimide

“…60−64 Furthermore, achiral 1,8-naphthalimide derivatives show helical fiber-like morphologies on gelation in a wide range of polar solvents, which are tunable by adding a chiral substrate such as tartaric acid through the formation of intermolecular H-bonds. 65 Besides, naphthalimides with chiral amino side chains are highly efficient artificial nucleases and antitumor agents, 66 serving as intercalators to DNA molecules. 67 On the other hand, solvent plays an important role in guiding different structural patterns of naphthalimide containing self-assemblies and affects their physical properties.…”

“…Self-assembled supramolecular systems usually show distinct properties compared to discrete molecules of the parent counterparts, , thus allowing exploration of various types of applications. − In particular, different supramolecular systems based on chiral organic molecules have found a recognized application in enantioselective catalysis − and molecular recognition , with biological relevance. Among such molecules, naphthalimides are of special interest due to their extensive use for constructing scaffolds for host–guest chemistry. − The advantage of such systems lies in the fact that the dipolar nature of cyclic aromatic imides controls their packing patterns in the solid state. − Owing to such dipolar interactions, a definite impetus exists to generate π-stacks of naphthalimide ligands with new structural patterns. − On the other hand, naphthalimide bearing compounds have found importance as sensors, optical materials, and in ion transports. − In addition, attaching a chiral unit to these systems provides avenues for new supramolecular synthons. − The ability of 1,8-naphthalimide derivatives to form strong intermolecular complexes with nucleic acids is also relevant to DNA cleavage. − Furthermore, achiral 1,8-naphthalimide derivatives show helical fiber-like morphologies on gelation in a wide range of polar solvents, which are tunable by adding a chiral substrate such as tartaric acid through the formation of intermolecular H-bonds . Besides, naphthalimides with chiral amino side...…”