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Saturated and unsaturated aliphatic side chain-appended naphthalenediimide derivatives: synthesis and structure property relationship

  • Polymers & biopolymers
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Abstract

Previous studies have shown influence of aliphatic side chain length and type on the transport properties of naphthalenediimide (NDI) materials by affecting molecular arrangement. There is lack of comparative study on the presence or absence of unsaturation in side chain and its effect on optical and electronic properties of NDI. The present work focuses on the structure–property relationship of four NDI derivatives bearing octyl (C8, OctA-NDI), hexadecyl (C16, HD-NDI), octadecyl (C18, ODA-NDI) and oleyl (C18-un, unsaturated, OLA-NDI) chain on imide-nitrogen. The self-assembling behaviour of the molecules is studied in concentrated solutions as fresh and aged samples in four different solvents by absorbance and emission spectroscopy. With increase in alkyl chain length, the aggregation behaviour is observed to increase. Very interestingly introduction of unsaturation in side chain reduces aggregation and restores the monomeric properties. Self-assembled microstructures formation was studied by scanning electron microscopy where all the four materials show different types of self-assembly formation. Finally, we compared the thermally activated electron conductivity and electron mobility of NDI derivatives, where also the side chain structure clearly influences the electron transport. Electron mobility decreases on increasing chain length from C8 to C18 and again increases in C18-un. A rationale for the structure–property relationship has been given based on the molecular packing and intermolecular π–π interactions. This study contributes significantly towards designing new NDI derivatives bearing long side chains with hampered aggregation for niche applications.

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Acknowledgements

MA acknowledges UGC for junior research fellowship. SN thanks CSIR for research associate fellowship to carry out the research. RK acknowledges DST for funding through SERD program (DST/TMD/CERI).

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Authors and Affiliations

  1. Photovoltaic Metrology Group, Advanced Materials and Devices Metrology Division, CSIR-National Physical Laboratory, National Measurement Institute of India, Dr. K. S. Krishnan Marg, New Delhi, 110012, India

    Mehak Ahuja, Neelam Kumari, Samya Naqvi & Rachana Kumar

  2. Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh, 201002, India

    Mehak Ahuja & Rachana Kumar

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  1. Mehak Ahuja
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  2. Neelam Kumari
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MA and NK made contributions towards investigation, formal analysis, validation and writing original draft. SN contributed for mobility measurements. Conceptualization, visualization, review and editing were contributed by RK.

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Correspondence to Rachana Kumar.

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Ahuja, M., Kumari, N., Naqvi, S. et al. Saturated and unsaturated aliphatic side chain-appended naphthalenediimide derivatives: synthesis and structure property relationship. J Mater Sci 56, 18327–18340 (2021). https://doi.org/10.1007/s10853-021-06502-z

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