Premium
Assembly‐Induced Diverse Optical Property of 4‐Biphenylcarboxy‐Protected Serine and Tyrosine
Author(s) -
Sasmal Supriya,
Podder Debasish,
Debnath Mintu,
Nandi Sujay Kumar,
Haldar Debasish
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902353
Subject(s) - stacking , supramolecular chemistry , hydrogen bond , chromophore , birefringence , crystallography , tyrosine , side chain , crystal structure , serine , intermolecular force , stereochemistry , chemistry , amide , materials science , molecule , photochemistry , organic chemistry , biochemistry , phosphorylation , polymer , physics , quantum mechanics
4‐biphenylcarboxy‐protected serine and tyrosine were synthesized and their crystal packing induced diverse optical properties in solid state were investigated. The L‐serine containing compound exhibits green‐gold birefringence under polarized light but the L‐tyrosine containing compound has no birefringence. Only L‐serine containing compound shows solid state emission at 525 nm. The crystal structure shows that irrespective of the π‐π stacking interactions between biphenyl moieties, the hydrogen bond between amide C=O and L‐serine side chain HO direct the supramolecular assembly to a parallel sheet like structure. But, the L‐tyrosine containing compound forms a supramolecular strand through intermolecular hydrogen bonds between ester C=O and L‐tyrosine side chain HO. Though the biphenyl moieties are in a parallel arrangement in the strand, there is no π‐π stacking interaction. Irrespective of biphenyl chromophore, the compounds exhibit different packing‐induced solid state optical properties.