Triptycene‐Based Organic Nanosheet Assemblies via Reversible Boronic Ester Formation: Alkyl Chain Length‐Dependent Formation and Aggregation
4 affiliations
- 1Center for Basic Research on Materials National Institute for Materials Science (NIMS) Tsukuba Ibaraki Japan
- 2Division of Materials Science Nara Institute of Science and Technology (NAIST) Ikoma Nara Japan
- 3Research Center for Macromolecules and Biomaterials National Institute for Materials Science (NIMS) Tsukuba Ibaraki Japan
- 4Institute for Chemical Research Kyoto University Uji Kyoto Japan
Abstract
A bottom‐up strategy for the preparation of triptycene‐based organic nanosheet assemblies through reversible boronic ester formation is presented. The triptycene scaffold enables the orthogonal placement of alkyl substituents and boronic ester‐forming sites, providing a molecular platform to examine how peripheral alkyl chains influence nanosheet formation and aggregation. Time‐dependent microscopy observations revealed alkyl‐chain‐length‐dependent assembly behavior. Hexyl‐substituted precursors afforded sheet‐like domains at an earlier stage, whereas methyl‐ and ethyl‐substituted analogs showed slower formation of less‐defined nanosheet‐like morphologies. These results indicate that longer alkyl chains are associated with earlier formation of sheet‐like domains and stronger aggregation; however, this alkyl‐chain effect is described as an empirical trend rather than a definitively established mechanism. Infrared spectroscopy supported boronic ester formation, and single‐crystal structures of partial molecular analogs confirmed the orthogonal arrangement of the alkyl substituents relative to the framework‐forming units. Absorption measurements showed a slight red‐shift for the nanosheet assemblies relative to the corresponding reference compounds, consistent with modest extension of electronic communication within the boronic ester‐linked framework. This study provides a case study showing that peripheral alkyl substituents can influence the formation and aggregation behavior of triptycene‐based organic nanosheet assemblies, offering useful insight into the development of dispersible 2D organic materials.
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BibTeX
@article{hayashi2026triptycenebased,
title = {{Triptycene‐Based Organic Nanosheet Assemblies via Reversible Boronic Ester Formation: Alkyl Chain Length‐Dependent Formation and Aggregation}},
author = {Hironobu Hayashi and Kizuku Yamamoto and Madhuparna Chakraborty and Junko Aimi and Nobuyuki Ishida and Naoki Aratani and Hiroko Yamada},
journal = {Chempluschem},
year = {2026},
month = oct,
doi = {10.1002/cplu.70276},
url = {https://doi.org/10.1002/cplu.70276},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Triptycene‐Based Organic Nanosheet Assemblies via Reversible Boronic Ester Formation: Alkyl Chain Length‐Dependent Formation and Aggregation
AU - Hironobu Hayashi
AU - Kizuku Yamamoto
AU - Madhuparna Chakraborty
AU - Junko Aimi
AU - Nobuyuki Ishida
AU - Naoki Aratani
AU - Hiroko Yamada
PY - 2026
DA - 2026/10/27
JO - Chempluschem
DO - 10.1002/cplu.70276
UR - https://doi.org/10.1002/cplu.70276
AB - A bottom‐up strategy for the preparation of triptycene‐based organic nanosheet assemblies through reversible boronic ester formation is presented. The triptycene scaffold enables the orthogonal placement of alkyl substituents and boronic ester‐forming sites, providing a molecular platform to examine how peripheral alkyl chains influence nanosheet formation and aggregation. Time‐dependent microscopy observations revealed alkyl‐chain‐length‐dependent assembly behavior. Hexyl‐substituted precursors afforded sheet‐like domains at an earlier stage, whereas methyl‐ and ethyl‐substituted analogs showed slower formation of less‐defined nanosheet‐like morphologies. These results indicate that longer alkyl chains are associated with earlier formation of sheet‐like domains and stronger aggregation; however, this alkyl‐chain effect is described as an empirical trend rather than a definitively established mechanism. Infrared spectroscopy supported boronic ester formation, and single‐crystal structures of partial molecular analogs confirmed the orthogonal arrangement of the alkyl substituents relative to the framework‐forming units. Absorption measurements showed a slight red‐shift for the nanosheet assemblies relative to the corresponding reference compounds, consistent with modest extension of electronic communication within the boronic ester‐linked framework. This study provides a case study showing that peripheral alkyl substituents can influence the formation and aggregation behavior of triptycene‐based organic nanosheet assemblies, offering useful insight into the development of dispersible 2D organic materials.
SN - 2192-6506
ER -