title: Molecular Architectonics of Naphthalenediimides for Efficient Structure-Property Correlation.
abstract: 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 cm(2) V(-1)s(-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.
authors.affiliation: Bioorganic Chemistry Laboratory, New Chemistry Unit (NCU), Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR) , Jakkur P.O., Bengaluru 560064, India.
authors.forename: M B
authors.initials: MB
authors.lastname: Avinash
authors.affiliation: Molecular Electronics Lab, Chemistry and Physics of Materials Unit (CPMU), Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR) , Jakkur P.O., Bengaluru 560064, India.
authors.forename: K
authors.initials: K
authors.lastname: Swathi
authors.affiliation: Molecular Electronics Lab, Chemistry and Physics of Materials Unit (CPMU), Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR) , Jakkur P.O., Bengaluru 560064, India.
authors.forename: K S
authors.initials: KS
authors.lastname: Narayan
authors.affiliation: Bioorganic Chemistry Laboratory, New Chemistry Unit (NCU), Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR) , Jakkur P.O., Bengaluru 560064, India.
authors.forename: T
authors.initials: T
authors.lastname: Govindaraju
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000235:genetics; D002942:Circular Dichroism; D004583:Electrons; D007094:Imides / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009154:Mutation; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry*; D010649:Phenylalanine / Q000737:chemistry; D012666:Semiconductors; D013329:Structure-Activity Relationship
chemical_list: D000596:Amino Acids; D007094:Imides; D009281:Naphthalenes; C542131:naphthalenediimide; D010649:Phenylalanine
keywords: electron mobility; molecular architectonics; organic semiconductors; self-assembly; structure−property correlation