journal article·2024-08-14

Ordered Carbonaceous Framework Synthesized from Hexaazatrinaphthylene with Enediyne Groups via Solid-State Bergman Cyclization Reaction

Yuki Sano, Ryojun Toyoda, Koki Chida, Takeharu Yoshii, Hirotomo Nishihara, Yuta Nishina, Daisuke Asanoma, Shinya Takaishi, Kunihisa Sugimoto, Ryota Sakamoto

ACS Applied Materials & Interfaces· Volume 16· Issue 32
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Abstract

Porous materials synthesized through bottom-up approaches, such as metal-organic frameworks and covalent organic frameworks, have attracted attention owing to their design flexibility for functional materials. However, achieving the chemical and thermal stability of these materials for various applications is challenging considering the reversible coordination bonds and irreversible covalent bonds in their frameworks. Thus, ordered carbonaceous frameworks (OCFs) emerge as a promising class of bottom-up materials with good periodicity, thermal and chemical stability, and electrical conductivity. However, a few OCFs have been reported owing to the limited range of precursor molecules. Herein, we designed a hexaazatrinaphthylene-based molecule with enediyne groups as a precursor molecule for synthesizing an OCF. The solid-state Bergman cyclization of enediyne groups at a low temperature formed a microporous polymer and an OCF, exhibiting redox activity and demonstrating their potential for electrochemical applications. The microporous polymer was used as an active material in sodium-ion batteries, while the OCF was used as an electrochemical capacitor. These findings illustrate the utility of the Bergman cyclization reaction for synthesizing microporous polymers and OCFs with a customizable functionality for broad applications.
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Research context

OpenAlex topics: Covalent Organic Framework Applications · Metal-Organic Frameworks: Synthesis and Applications · Synthesis and Properties of Aromatic Compounds

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aza-Aoba, Aramaki, Sendai 980-8578, Japan

Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-1-1 Katahira, Aoba, Sendai, Miyagi 980-8577, Japan

Advanced Institute for Materials Research (WPI-AIMR), Tohoku University, 2-1-1 Katahira, Aoba, Sendai, Miyagi 980-8577, Japan

Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan

Research Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan

Department of Chemistry, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan

Division for the Establishment of Frontier Sciences of Organization for Advanced Studies at Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan

Funding

Nippon Sheet Glass Foundation for Materials Science and Engineering · Ministry of Education, Culture, Sports, Science and Technology · Asahi Glass Foundation · Fusion Oriented REsearch for disruptive Science and Technology

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