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Pathway Diversity Leads to 2D‐Nanostructure in Photo‐triggered Supramolecular Assembly
Author(s) -
Pal Deep Sankar,
Ghosh Suhrit
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800888
Subject(s) - carboxylic acid , monomer , stacking , chromophore , supramolecular chemistry , chemistry , diimide , derivative (finance) , self assembly , photochemistry , materials science , polymer chemistry , molecule , organic chemistry , polymer , perylene , financial economics , economics
This Communication reports photo‐triggered supramolecular assembly of a naphthalene‐diimide (NDI) derivative, appended with a photo‐labile ortho ‐nitrobenzyl (ONB)‐ester protected carboxylic acid. Photo‐irradiation produces the free COOH group which facilitates H‐bonding‐driven face‐to‐face stacking of the NDI chromophores producing an ultra‐thin (height <2.0 nm) two‐dimensional (2D) nanosheet. In contrast, spontaneous supramolecular assembly of the same active monomer exhibits entirely different features such as uncontrolled growth, J‐aggregation and fibrillar morphology. A completely different pathway for photo‐triggered assembly is attributed to the dual function of the photo‐caged pro‐monomer in i) producing the carboxylic acid in controlled manner and ii) simultaneously inhibiting the spontaneous J‐aggregation of the photo‐generated monomers by ester‐carboxylic acid H‐bonding and in turn directing a distinct growth mechanism.