The Chuang Research Group
Department of Applied Chemistry, National Yang Ming Chiao Tung University
Hsinchu, Taiwan
We work on development of new synthetic methodology with focus on phosphine-mediated reaction and transition-metal catalyzed C-H bond activation. The developed methodology can be further demonstrated toward synthesis of novel fullerene C60/C70 derivatives for application in the organic solar cells.
Our research program:
1. Educate and mentor students
2. Broaden students' scientific viewpoints
3. Lead students to uncover questions and solve significant questions by scientific approaches
Research topics:
1. Conjugate alpha-addition reaction
2. Transition-metal-catalyzed C-H bond activation
Rajeshkumar, V.; Lee, T.-H.; Chuang, S.-C.* Org. Lett. 2013, 15, 1468.
3. Organic photovoltaics
4. Fullerene C60/C70 chemistry
Recent publication
Cascade One-Pot Synthesis of Orange-Red Fluorescent Polycyclic Cinnolino[2,3-f]phenanthridin-9-ium Salts by Palladium(II)-Catalyzed C-H Bond Activation of 2-Azobiaryls and Alkenes
Jayachandran Jayakumar, Guganchandar Vedarethinam, Huan-Chang Hsiao, Shang-You Sun and Shih-Ching Chuang*
Angew. Chem. Int. Ed. 2020, 59, 689-694.
Abstract: The first palladium-catalyzed synthesis of quaternary ammonium salts through double oxidative C-H bond activation on azobenzenes in moderate to good yields is reported. In this study, we disclose a highly regioselective synthesis of orange-red fluorescent cinnolino[2,3-f]phenanthridin-9-ium salts and 15H-cinnolino[2,3-f]phenanthridin-9-ium-10-ide from 2-azobiaryls and alkenes catalyzed by palladium(II). The reaction mechanism is proposed involving an ortho C-H olefination of 2-azobiaryls with alkenes, intramolecular aza-Michael addition, concerted metalation deprotonation (CMD), reductive elimination and oxidation.
Palladium‐Catalyzed Benzofulvenation of o‐Arylanilines through C−H Bond Activation by Using Two Diarylacetylenes as an Implicit Benzofulvene
Selvam Raju, Huan-Chang Hsiao, Selvakumar Thirupathi, Pei-Ling Chen, and Shih-Ching Chuang*
Adv. Synth. Catal. 2019, 361, 683-689.
Abstract: We report the first example of Pd(II)‐catalyzed highly step‐ and atom‐economical benzofulvenation through free amine‐directed ortho C−H bond activation of o‐arylanilines. This paper presents a novel, simple, and efficient approach for the synthesis of benzofulvene derivatives from o‐arylaniline substrates through C−H bond activation with two diarylacetylenes as an implicit benzofulvene unit. The reactivity of synthesized benzofulvenes toward oxidation was investigated, and they were shown to transform into phenanthridines, oxabenzofulvenes, and fluorescent polycyclics.
Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates
Pratheepkumar Annamalai and Shih-Ching Chuang* et al
Org. Lett. 2019, 21, 1182-1186.
Abstract
A palladium-catalyzed C–H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C–H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a'/anti-3a' = 36:64) from multiple C–H bond functionalizations. Additionally, nondirected C–H bond functionalization at the C-4' position with alkenes rendered complete C–H functionalization of five C–H bonds that formed a stable hexa-substituted benzene ring.
Organic bulk heterojunction photovoltaics incorporating cyclopenteno[60]fullerene monoadducts as n-type materials display superior power conversion efficiency than with PC61BM
Po-Yen Tseng,† Huan-Chang Hsiao,† Cheng-Ming Hsieh,† An-Ju Wu, and Shih-Ching Chuang*
J. Chin. Chem. Soc. 2020, 67, 430.
Abstract
Organic bulk heterojunction photovoltaics, merely incorporating monoadducts of cyclopenteno[60]fullerenes (CPFs) as n‐type materials and P3HT as p‐type materials, display superior power conversion efficiency up to 4.6 ± 0.12%, superseding that with PC61BM/P3HT (3.8 ± 0.20%) for ca. 20%, under AM 1.5G irradiation―primarily attributed to the lack of homo‐conjugation on CPFs and their higher LUMO energy levels.