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This study introduces the synthesis and detailed self\u2010assembly analysis of tetraphenylethylene (<jats:bold>TPE<\/jats:bold>) functionalized naphthalene diimide (<jats:bold>NDI<\/jats:bold>), a novel donor\u2010acceptor molecular structure referred to as <jats:bold>TPE\u2010NDI<\/jats:bold>. The investigation specifically focuses on elucidating the self\u2010assembly behavior of <jats:bold>TPE\u2010NDI<\/jats:bold> in mixed solvents of varying polarities, namely chloroform: methylcyclohexane (CHCl<jats:sub>3<\/jats:sub>: MCH) and chloroform: methanol (CHCl<jats:sub>3<\/jats:sub>: MeOH). Employing a several analytical methodologies, including UV\u2010Vis absorption and fluorescence emission spectroscopy, scanning electron microscopy (SEM), X\u2010ray diffraction (XRD), and dynamic light scattering (DLS), these self\u2010assembled systems have been comprehensively examined. The results reveal that <jats:bold>TPE\u2010NDI<\/jats:bold> manifests as distinct particles in CHCl<jats:sub>3<\/jats:sub>: MCH (<jats:italic>f<\/jats:italic><jats:sub>MCH<\/jats:sub>=90\u2009%), while transitioning to flower\u2010like assemblies in CHCl<jats:sub>3<\/jats:sub>: MeOH (<jats:italic>f<\/jats:italic><jats:sub>MeOH<\/jats:sub>=90\u2009%). This finding underscores the critical role of solvent polarity in dictating the morphological characteristics of <jats:bold>TPE\u2010NDI<\/jats:bold> self\u2010assembled aggregates. Furthermore, the study proposes a molecular packing mechanism, based on SEM data, offering significant insights into the design and development of functional supramolecular systems. Such advancements in understanding the molecular self\u2010assembly new \u03c0\u2010conjugated molecular structures are anticipated to pave the way for novel applications in material science and nanotechnology.<\/jats:p>","DOI":"10.1002\/asia.202301046","type":"journal-article","created":{"date-parts":[[2024,1,5]],"date-time":"2024-01-05T06:13:18Z","timestamp":1704435198000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis, Photophysical Properties and Self\u2010Assembly of a Tetraphenylethylene\u2010Naphthalene Diimide Donor\u2010Acceptor Molecule"],"prefix":"10.1002","volume":"19","author":[{"given":"Dnyaneshwar I.","family":"Bhusanur","sequence":"first","affiliation":[{"name":"Polymers and Functional Materials Division CSIR-Indian Institute of Chemical Technology  500\u2009007 Hyderabad Telangana India"},{"name":"Academy of Scientific and Innovative Research (AcSIR)  201\u2009002 Ghaziabad Uttar Pradesh 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