Simple Organic Salts Having a Naphthalenediimide (NDI) core display multifunctional properties: Gelation, anticancer and semiconducting properties

Abstract

Following a supramolecular synthon rationale, a dicarboxylic acid derivative having a naphthalenediimide (NDI) core, namely, bis-N-carboxymethyl naphthalenediimide (NDI-G), was reacted with n-alkyl amines with varying alkyl chain lengths to generate a new series of primary ammonium dicarboxylate (PAD) salts. The majority of the salts (≈85 %) were found to gel various polar solvents. The gels were characterized by dynamic rheology and high-resolution electron microscopy. Single-crystal and powder X-ray diffraction analyses were used to study the supramolecular synthon present in one of the gelator salts (i.e., S8). Charge-transfer (CT)-induced gelation with donor molecules such as anthracene methanol (Ant) and pyrene (Py) was also possible with S8. The CT complex (S8.Ant) displayed anticancer activity as probed by cell migration assay on the highly aggresive breast cancer cell line MDA-MB-231. The DMSO gel of S8.Ant also displayed semiconducting behavior. To the best of our knowledge, simple organic salts with an NDI core that display such mulitifunctional properties are hitherto unknown.