課題番号 ：S-16-NM-0047
利用形態 ：機器利用
利用課題名（日本語） ：刺激応答性π電子系集合体の開発
Program Title (English) ：Development of Stimuli-Responsive -Conjugated Molecular Assemblies
利用者名（日本語） ：デビー・リー
Username (English) ：Debbie Le
所属名（日本語） ：ブリティッシュコロンビア大学大学院化学科
Affiliation (English) ：Department of Chemistry, University of British Columbia

１．概要（Summary）
A target functionalized naphthalenediimide compound with self-assembly promoting side chains was successfully synthesized after five reaction steps. The synthesis of a reference compound to be used as a comparison to the target compound was also confirmed. The structure and purity of both final compounds were confirmed by 1H NMR and 13C NMR spectroscopy. Finally, UV-Visible spectroscopy was used to determine molar absorptivity and the mode of self-assembly of the new supramolecular building blocks.

２．実験（Experimental）
【利用した主な装置】
 核磁気共鳴装置（NMR）

３．結果と考察 （Results and Discussion）
Naphthalene diimides (NDIs) are imide-based aromatic compounds known to form n-type organic semiconductor materials or supramolecular assemblies, and be used in applications including catalysis, biomedicine, and electronics. The electron-deficient π-system allows NDI to form donor-acceptor conjugates when combined with electron donating groups. The molecular structure of NDI (Figure 1) is also useful for creating organic materials since the planar, rigid structure may lead to stacking in solution or the solid state, and various substituents may be introduced on the naphthalene core or imide-nitrogens to tune the electronic properties.

Figure 1: General structure of naphthalene diimides

Previously in our group, an unusual reaction between a functionalized naphthalene diimide molecule and an amine to form a donor-acceptor complex was discovered. Upon amine addition to form a donor-acceptor complex, the appearance of a strong charge transfer band was also observed by UV-visible spectroscopy. Inspired by this new reaction, the formation of supramolecular assemblies with functionalized NDI compounds was investigated to explore an analogous reaction in a supramolecular architecture. In pursuit of a functionalized naphthalene diimide compound that would act as a building block for supramolecular assemblies, the synthesis was carried out. A functionalized NDI backbone was linked to amides, which are known to promote one-dimensional supramolecular aggregation of NDIs via hydrogen bonding at the amide functionalities and van der Waals interactions through the long alkyl chains.

４．その他・特記事項（Others）
Facility staff assisted me to use NMR.
５．論文・学会発表（Publication/Presentation）
なし
６．関連特許（Patent）
なし