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  4. Functional Organic Chemistry

Functional Organic Chemistry

Staff & Contact

Educational Staff Prof. Hiroko Yamada
Associate Prof. Naoki Aratani
Assist prof.Hironobu Hayashi, Kyohei Matsuo
Contact TEL: +81-743-72-6041
URL https://mswebs.naist.jp/LABs/env_photo_greenmat/en/Yamada_Group/HOME.html

Education and Research Activities in the Laboratory

The Photofunctional Organic Chemistry Laboratory was established on January 1, 2011 then changed to "Functional Organic Chemistry" in 2021 to reflect the broader scope of research. We focus on the development of functional organic materials including organic semiconductors for photovoltaic cells and organic thin-film transistors, highly fluorescent dyes, etc. on the basis of organic synthesis. In particular, acenes and porphyrinoids are our current target compounds. Students at our laboratory are encouraged to work independently and freely on their own original research themes.

Research Themes

1. Development of high-performance molecular semiconductors for solution-processed organic electronic devices

We are trying to engineer well-performing organic semiconducting thin films for use in electronic devices such as organic field effect transistors. To this end, we employ a unique deposition technique called "precursor approach" (Fig. 1), and are preparing new compounds (Fig. 2)--typically derivatives of acenes and benzoporphyrin--that can be processed by this method (Fig. 3).

2. Development of graphene nanoribbons

We are investigating the surface-assisted graphene nanoribbon (GNR) synthesis that allows width, edge structure, and heteroatom incorporation to be modulated with atomic-level precision (Fig. 4). Our group is currently involved in, among others, collaborative projects of "Tailor-Made Synthesis of Graphene Nanoribbons for Innovative Devices" (JST CREST).

3. Creation of unique carbon frameworks with remarkable optical/electronic properties

We have created various novel functional polycyclic aromatic hydrocarbons (PAHs). These compounds have near-infrared absorption properties, intensive light emission, or excellent redox properties. For instance, a remarkably strained cyclopyrenylene trimer was synthesized and it underwent the first biaryl C-C σ-bond cleavage with 1O2 (Fig. 5)



A photoprecursor method for the longest acene "nonacene" synthesis

Fig. 2

An organic semiconducting thin-film for use in OFET devices

Fig. 3

Photo-irradiation process on making of organic thin-film devices

Fig. 4

On-surface synthesis of graphene nanoribbon (GNR)

Fig. 5

A high-strained cyclopyrenylene trimer

Recent Research Papers and Achievements

1. H. Hayashi, H. Yamada, R. Fasel et al., On-surface light-induced generation of higher acenes and elucidation of their open-shell character, Nat. Commun., 2019, 10, 861.
2. K. Takahashi, M. Suzuki, Q. Miao, H. Yamada et al., Engineering Thin Films of a Tetrabenzoporphyrin toward Efficient Charge-Carrier Transport: Selective Formation of a Brickwork Motif, ACS Appl. Mater. Interfaces, 2017, 9, 8211.
3. J. Yamaguchi, H. Hayashi, H. Yamada, S. Sato et al., Small bandgap in atomically precise 17-atom-wide armchair-edged graphene nanoribbons, Commun. Mater., 2020, 1, 36.
4. R. Kurosaki, H. Hayashi, M. Suzuki, J. Jiang, M. Hatanaka, N. Aratani, H. Yamada, A remarkably strained cyclopyrenylene trimer that undergoes metal-free direct oxygen insertion into the biaryl C-C σ-bond, Chem. Sci., 2019, 10, 6785. (Selected as an Inside Back Cover)