Molecular Architectonics of Naphthalenediimides for Efficient Structure–Property Correlation

• Published in: ACS applied materials & interfaces 2016-04, Vol.8 (13), p.8678-8685
• Main Authors: Avinash, M. B, Swathi, K, Narayan, K. S, Govindaraju, T
• Format: Article
• Language: English
• Subjects: Amino Acids - chemistry; Amino Acids - genetics; Circular Dichroism; Electrons; Imides - chemical synthesis; Imides - chemistry; Molecular Structure; Mutation; Naphthalenes - chemical synthesis; Naphthalenes - chemistry; Phenylalanine - chemistry; Semiconductors; Structure-Activity Relationship
• ISSN: 1944-8244; 1944-8252
• DOI: 10.1021/acsami.6b00011

We present a bioinspired design strategy to effectively tailor the assembly of naphthalenediimides (NDIs) into a wide variety of architectures by functionalizing with amino acid derivatives. This bioinspired process of custom designing and engineering molecular assemblies is termed “bioinspired architectonics”. By employing minute structural mutations in the form of α-substituents of amino acids, we successfully engineered molecular assembly of NDIs into zero-dimensional (0D, spheres), one-dimensional (1D, fibers), and two-dimensional (2D, sheets) architectures. The 2D sheets of phenylalanine methylester appended NDI 1 showed remarkable bulk electron mobility of up to 1 cm2 V–1s–1. With the aid of photophysical, diffraction, and microscopy techniques we rationalize the effect of molecular structure with their ordering and electronic properties in an effort to find structure–property correlations via a bioinspired modular approach.