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Insights into the AIEE of 1,8-Naphthalimides (NPIs): Inverse Effects of Intermolecular Interactions in Solution and Aggregates

Mukherjee, Sanjoy and Thilagar, Pakkirisamy (2014) Insights into the AIEE of 1,8-Naphthalimides (NPIs): Inverse Effects of Intermolecular Interactions in Solution and Aggregates. In: CHEMISTRY-A EUROPEAN JOURNAL, 20 (26). pp. 8012-8023.

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Official URL: http://dx.doi.org/10.1002/chem.201304694


Systematic structural perturbation has been used to fine-tune and understand the luminescence properties of three new 1,8-naphthalimides (NPIs) in solution and aggregates. The NPIs show blue emission in the solution state and their fluorescence quantum yields are dependent upon their molecular rigidity. In concentrated solutions of the NPIs, intermolecular interactions were found to quench the fluorescence due to the formation of excimers. In contrast, upon aggregation (in THF/H2O mixtures), the NPIs show aggregation-induced emission enhancement (AIEE). The NPIs also show moderately high solid-state emission quantum yields (ca. 10-12.7 %). The AIEE behaviour of the NPIs depends on their molecular rigidity and the nature of their intermolecular interactions. The NPIs 1-3 show different extents of intermolecular (pi-pi and C-H center dot center dot center dot O) interactions in their solid-state crystal structures depending on their substituents. Detailed photophysical, computational and structural investigations suggest that an optimal balance of structural flexibility and intermolecular communication is necessary for achieving AIEE characteristics in these NPIs.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to the WILEY-V C H VERLAG GMBH, BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY
Keywords: aggregation; density functional calculations; fluorescence; stacking interactions
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited: 14 Aug 2014 09:50
Last Modified: 14 Aug 2014 09:50
URI: http://eprints.iisc.ac.in/id/eprint/49544

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