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Synthesis and Binding Affinity of Hydrophobic Tail Containing Naphthalene Derivatives with Different Type of Organized Media
Author(s) -
Mani Pavnesh,
Pandey Anjani Kumar,
Tripathi Alok Kumar
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904460
Subject(s) - chemistry , hydrophobic effect , micelle , fluorophore , sodium dodecyl sulfate , naphthalene , hydrophobe , pulmonary surfactant , critical micelle concentration , aggregation number , aqueous solution , molecule , bromide , organic chemistry , fluorescence , biochemistry , physics , quantum mechanics
In this article, we are introducing the synthesis of two naphthalene derivatives ( NPBU (butyl 2‐(naphthalene‐2‐yl)acetate) and NPME (methyl 2‐(naphthalene‐2‐yl)acetate)) having different length of aliphatic tail. These two newly synthesized naphthalene derivative are used as a fluorophore to understand the binding interaction with surfactants (SDS (sodium dodecyl sulfate), CTAB (cetrimonium bromide) and Triton X‐100) and also with β ‐CD ( β ‐cyclodextrin). Because of long hydrophobic tail, NPBU is more hydrophobic in nature and showed self‐aggregation properties in aqueous medium. Whereas, the short aliphatic tail containing NPME not showed any self‐aggregation property in an aqueous medium. Because of hydrophobicity NPBU could binds with the hydrophobic inner core of micelles of SDS, CTSB and Triton X‐100. NPBU also formed inclusion complex with inner hydrophobic cavity of β ‐CD. However, because of low hydrophobicity NPME , could not able to binds with hydrophobic inner core of micelles and also it was not able to bind with hydrophobic cavity of β ‐CD. The calculated CMC (critical micelle concentration) values of SDS, CTAB and Triton X‐100 by using NPBU fluorophore are ∼12 mM, ∼0.8 mM and ∼0.12 mM respectively. The NPME binds with β ‐CD and formed inclusion complexes NPBU@ β ‐CD and calculated binding constant was 0.22 × 10 2 M −1 . Thus this presented comparative study is showing the importance of a hydrophobic tail, attached to naphthalene molecule. The attachment of a long hydrophobic tail makes the fluorophore sensitive towards microenvironment of surfactants and make naphthalene molecules suitable for investigation of structure and dynamics of micellization of different types of surfactants.