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Novel Pentadecyl Phenol‐Tagged L‐Tryptophan Molecules: Synthesis, Self‐ Assembly and Liquid Crystalline Properties
Author(s) -
Parappurath Akhil,
Abraham Jancy Nixon
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702171
Subject(s) - molecule , amide , hydrogen bond , amine gas treating , chemistry , tryptophan , self assembly , methanol , fluorescence , crystallography , polymer chemistry , organic chemistry , amino acid , biochemistry , physics , quantum mechanics
Abstract The paper describes the self‐assembly and liquid crystalline properties of pentadecylphenol tagged L‐tryptophan molecules having ester and amide functionality. We have synthesized a series of molecules having mono and ditryptophan moieties attached to pentadecylphenol through amide or ester linkage. The fluorescence properties of the Boc‐L‐tryptophan‐pentadecylphenol molecules were measured in methanol and found to aggregate beyond the critical aggregation concentration and self‐assembled to give spherical structures. Upon deprotection of Boc group, the amine end group got involved in extended hydrogen bonding and fibril like structures were developed. These molecules also showed liquid crystalline behavior in hydrogen bonding solvents such as benzyl alcohol and showed needle like crystals in tert‐butanol, as analyzed by polarized optical light microscopy.