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Effect of Slip‐Stack Self‐Assembly on Aggregation‐Induced Emission and Solid‐State Luminescence in 1,3‐Diarylpropynones
Author(s) -
Sivalingam Soumya,
Debsharma Kingshuk,
Dasgupta Ayan,
Sankararaman Sethuraman,
Prasad Edamana
Publication year - 2019
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201900024
Subject(s) - stacking , intramolecular force , photoluminescence , luminescence , quantum yield , molecule , aggregation induced emission , monomer , chemistry , slip (aerodynamics) , conjugated system , materials science , stack (abstract data type) , photochemistry , chemical physics , optoelectronics , stereochemistry , fluorescence , organic chemistry , physics , optics , computer science , polymer , thermodynamics , programming language
Co‐facial stacking can result in aggregation‐caused quenching (ACQ) in conjugated organic luminogens. This study provides an attractive ‘slip‐stack’ self‐assembly approach which can eliminate the occurrence of ACQ. The obtained results from steady‐state and time‐resolved optical studies, along with X‐ray diffraction and computational studies demonstrate aggregation‐induced emission enhancement (AIEE) of a donor‐π‐acceptor based 1,3‐diarylpropynone, namely 1‐(naphthalenyl)‐3‐(pyren‐1‐yl)prop‐2‐yn‐1‐one (PYNAP). Unlike the monomer, which exhibits poor photoluminescence in solution (φ f =2 % in ACN), the twisted manifold of PYNAP allows the orientation of the molecules in a slip‐stack fashion during the course of aggregation, which not only avoids a direct co‐facial arrangement, but also induces augmented rigidity, leading to restricted intramolecular rotation (RIR) and enhanced emission quantum yield (φ f =5 % in ACN/H 2 O). The aggregation behavior of PYNAP's congener, 1‐phenyl‐3‐(pyren‐1‐yl)prop‐2‐yn‐1‐one (PYPH) reinforces the hypothesis that slip‐stack assembly is a useful strategy for AIEE in polycyclic hydrocarbon luminogens.