研究者詳細 - 小林　透威

小林　透威（コバヤシ　トオイ）

Kobayashi, Toi

写真a

所属（所属キャンパス）: 薬学部薬科学科（芝共立）

職名: 助教

Scopus 論文情報

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Oxa-TriQuinoline: A New Entry to Aza-Oxa-Crown Architectures

Kobayashi T., Kumagai N.

Angewandte Chemie - International Edition 62 （ 32 ） 2023年08月

研究論文（学術雑誌）, 共著, 筆頭著者, 査読有り, ISSN 14337851

　概要を見る

A new 15-membered-macrocyclic molecular entity, oxa-TriQuinoline (o-TQ), was designed and synthesized. In o-TQ, three oxygen atoms were joined onto three quinoline units at the 2- and 8-positions in a head-to-tail fashion by three-fold SNAr reactions, giving rise to the characteristic N3O3 aza-oxa-crown architecture. o-TQ can serve as a new tridentate nitrogen ligand to capture a CuI cation and adopt a bowl shape, before supramolecular complexation with corannulene and [12]cycloparaphenylene (CPP) occurs through π–π and CH–π interactions. In the presence of the CuI cation, the non-emissive o-TQ becomes a highly emissive material in the solid state, whereby the emission wavelengths depend on the ancillary ligand on the CuI cation. The o-TQ/CuI complex is able to promote carbene catalysis to provide a range of enamines with a gem-difluorinated terminus.
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iso-TEtraQuinoline (i-TEQ): an inherently chiral N4 macrocyclic quinoline tetramer

Yagami R., Xu W., Kobayashi T., Nagata Y., Kumagai N.

Chemical Science 16 （ 24 ） 10714 - 10721 2025年05月

研究論文（学術雑誌）, 共著, 査読有り, ISSN 20416520

　概要を見る

Chiral macrocycles are attracting growing interest due to their broad applicability as ligands in asymmetric catalysis and as host molecules for chiral recognition. Robustness and high thermodynamic stability can be effectively achieved by strategically linking aromatic panels to construct an axially chiral macrocyclic framework. Cyclic concatenation of four quinoline units affords a fully sp<sup>2</sup>-hybridized, non-planar macrocycle featuring four inwardly oriented, coordinatively active pyridyl nitrogen atoms. The previously reported tetramer TEtraQuinoline (TEQ) exhibits head-to-tail connectivity of its quinoline units, affording an achiral architecture possessing S<inf>4</inf> symmetry. Herein, we report the design and synthesis of iso-TEtraQuinoline (i-TEQ), an inherently chiral analogue featuring head-to-head connectivity at the 2,2′- and 8,8′-positions, which gives rise to a D<inf>2</inf>-symmetric architecture. Detailed comparative investigations of the connectivity isomers i-TEQ and TEQ revealed an array of distinct characteristics, including the overall architecture, intrinsic macrocyclic strain, spatial orientation of nitrogen lone pairs, thermodynamic stability, racemisation behaviour, metal complex stability, and circularly polarised luminescence.
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Insights into Coordination and (Semi-)Rigidity in the Molecular Design of Bicyclic Heterocycle Frameworks

Kobayashi T.; Takuya S.; Naoya K.

Chemistry Letters 2026年

研究論文（学術雑誌）, 共著, 筆頭著者, 査読有り

　概要を見る

Macrocyclic compounds, exhibiting unique properties arising from their large-ring frameworks, have captivated the attention of organic chemists over the last few decades. These molecules serve specific functions across disciplines, including synthetic chemistry, materials science, and biology. Representative molecules in this category, including crown ethers, calix[n]arenes, and porphyrinoids composed of ether/phenol/pyrrole subunits, exhibit unparalleled structural and functional diversity. In contrast, macrocycles exploiting quinoline/quinazoline as key building blocks to construct specific macrocyclic architectures have received limited attention and are much less explored. In this Highlight Review, we summarize our recent advances in oligo-quinoline/quinazoline macrocycles. Emphasis is focused on synthetic strategies, structural features, and emerging applications in organometallic, supramolecular, and photophysical chemistry. We anticipate that these collective results will guide new molecular designs within the broader family of heterocycle-based macrocycles.
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Enlarged-TriQuinoline (Enl-TQ): Disparity in Chemical Behaviors by Geometric Scaling of the Trimeric Quinoline Ring System

Yamashita M., Tsutsumi R., Kobayashi T., Kumagai N.

Chemistry an Asian Journal 20 （ 17 ） 2025年

研究論文（学術雑誌）, 共著, 査読有り, ISSN 18614728

　概要を見る

TriQuinoline (TQ), a quasi-planar cyclic quinoline trimer concatenated at the 2,8-positions in a head-to-tail arrangement, strongly captures a proton at the 12-membered inner cycle and exhibits unusual physicochemical properties, including unexpected water solubility and the ability to engage in complexation with other π-conjugated molecules. In this study, we designed and synthesized its expanded analog, coined Enlarged-TriQuinoline (Enl-TQ), in which three alkyne units are embedded between three quinoline units to acquire an expanded planar 18-membered ring system. DFT calculations and X-ray crystallographic analysis revealed its planar architecture with three inwardly facing pyridinic nitrogen atoms. Despite its structural similarity to TQ, Enl-TQ displayed distinct host capability and photophysical characteristics.
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Development of Unique Quinoline-Based Macrocyclic Systems and Strategic Applications in Versatile Chemistry

Kobayashi T., Xu W., Kumagai N.

Yuki Gosei Kagaku Kyokaishi 83 （ 5 ） 386 - 394 2025年

研究論文（学術雑誌）, 共著, 筆頭著者, 査読有り, ISSN 00379980

　概要を見る

Macrocyclic compounds exhibit unique properties due to their large ring─shaped structures, which have captivated chemists in recent decades. These molecules exert specific functions in a multidisciplinary basis, e.g. chemistry, materials science, and biology. Crown ethers, calix [n] arenes, and porphyrinoids, which contain several ether／phenol／pyrrole subunits, represent milestones in these molecular categories with unparalleled functional diversity. In contrast, macrocycles exploiting quinoline as a key unitary element to construct specific macrocyclic architecture have received limited attention and been barely explored. In this report, we summarize the recent advances in oligo─ quinoline macrocycles TriQuinoline (TQ), oxa─TriQuinoline (o─TQ), TEtraQuinoline (TEQ), and indole／quinoline hybrid macrocycle In2Q2. Particular emphasis is placed on the synthesis, structure, and application of these molecules in organometallic and supramolecular chemistry, which may guide new molecular designs in the heterocycle─based macrocycle family.
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酸素原子ドープドキノリンオリゴマー群の合成と多座配位子としての機能開拓

小林透威

[国内会議] ２０２５年度関東支部若手研究者のためのセミナー（東京） ,

2025年08月
,
口頭発表（招待・特別）
トリポーダル型oxa-TriQuinoline (o-TQ) 配位子によるCuカルベン挿入反応の高活性化

小林透威，熊谷直哉

[国内会議] 日本薬学会第146年会（大阪） ,

2026年03月
,
ポスター発表
キノリン環を組み込んだ窒素ドープ型カーボンナノリングの合成

山下舞，小林透威，熊谷直哉

[国内会議] 日本薬学会第146年会（大阪） ,

2026年03月
,
口頭発表（一般）
キノリン環を組み込んだ窒素ドープ型カーボンナノリングの合成

山下舞，小林透威，熊谷直哉

[国内会議] 日本化学会第106春季年会（2026）（千葉） ,

2026年03月
,
口頭発表（一般）
窒素原子架橋型キノリン3量体aza-TriQuinoline（a-TQ）の合成

中森佳亮，根本春美，小林透威，熊谷直哉

[国内会議] 日本化学会第106春季年会（2026）（千葉） ,

2026年03月
,
ポスター発表