Aggregation-Induced Emission of Naphthalene Diimides: Effect of Chain Length on Liquid and Solid-Phase Emissive Properties

Alberto Insuasty; Serena Carrara; Jiao Xuechen; Christopher R McNeill; Conor Hogan; Steven J Langford

doi:10.1002/asia.202400152

Aggregation-Induced Emission of Naphthalene Diimides: Effect of Chain Length on Liquid and Solid-Phase Emissive Properties

Chem Asian J. 2024 Mar 25:e202400152. doi: 10.1002/asia.202400152. Online ahead of print.

Authors

Alberto Insuasty^{1

2}, Serena Carrara³, Jiao Xuechen⁴, Christopher R McNeill⁴, Conor Hogan³, Steven J Langford^{1

5}

Affiliations

¹ Department of Chemistry and Biotechnology, Swinburne University of Technology, Hawthorn, VIC 3122, Australia.
² Grupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad del Valle, Calle 13 # 100-00, Cali, 760032, Colombia.
³ La Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC 3086, Australia.
⁴ Department of Materials Science and Engineering, Monash University, Melbourne, VIC 3080, Australia.
⁵ School of Mathematical and Physics Sciences, University of Technology Sydney, Ultimo, NSW 2007, Australia.

PMID: 38528740
DOI: 10.1002/asia.202400152

Abstract

The aggregation-induced emission (AIE) properties of a systematic series of naphthalene diimides (NDIs) varying the chain length at the imide positions have been studied. A solvophobic collapse of NDI units through the flash injection of THF NDI solutions in sonicating water triggers the formation of stable suspensions with enhanced fluorescence emissions. Shorter chains favor the π-π stacking of NDI units through H-aggregation producing a strong AIE effect showing remarkably high quantum yields that have not been observed for non core-substitued NDIs previously. On the other hand, NDIs functionalized with longer chains lead to more disordered domains where π-π stacking between NDI units is mainly given by J-aggregation unfavoring the AIE effect.

Keywords: Aggregation-Induced Emission; H-aggregates; J-aggregates; Naphthalene Diimides; π-π stacking.

Abstract

Grants and funding