Professor Shih-Ching Chuang

1. 1. Chen, S.-H.; Chen, Y.-L.; Chen, C.-Y.; Wu, C.-S.; Su, M.-D.*; Chuang, S.-C.* “Spirocyclopropanes and Substituted Furans by Controlling Reactivity of 1,3-Enynoates: γ- and δ-Addition of Phosphines to Conjugate Acceptors” Chem. Eur. J. 2024, 30, e202402688 . https://doi.org/10.1002/chem.202402688
   2. Wang, W.-Q.; Nallapati, S.; Chen, C.-Y.; Yaoita, T.; Yamaoka, S.; Murata, M.*; Chuang, S.-C.* “Phosphine-promoted synthesis of naphthoquinones fused with cyclopentadienyl moiety via ring expansion: synthesis, reactivity, and ring contraction via [1,5] sigmatropic rearrangement“ Org. Lett. 2024, 26, 8730-8735.
   3. Hsiao, H.-C.; Li, M.-C.; Vedarethinam, G.; Chen, P.-L.; Chuang, S.-C.* “Synthesis of Benzo[c]cinnolinium Salts from 2-Azobiaryls by Copper(Ⅱ) or Electrochemical Oxidation” Org. Lett. 2024, 26,1694-1698. Open Access Link: https://pubs.acs.org/doi/full/10.1021/acs.orglett.4c00213
   4. Hsiao, H.-C.; Chen, P.-L.; Chuang, S.-C.* “Synthesis and Photophysical Properties of Fluorescent Benzo[def]carbazoles” J. Chin. Chem. Soc. 2023, 70, 1591-1598.
   5. Jayabal, K.*; Elumalai, D.; Leelakrishnan, S.; Bhattacharya, S.; Rengarajan, V.; Kannan, T.; Chuang, S.-C.* “Green and Regioselective Approach for the Synthesis of 3-Substituted Indole Based 1,2-Dihydropyridine and Azaxanthone Derivatives as a Potential Lead for SARS-CoV-2 and Delta Plus Mutant Virus: DFT and Docking Studies” ACS Omega 2022, 7, 43856-43876.
   6. Ueda, K.; Fukuzaki, R.; Ito, T.; Toyama, N.; Muraoka, M.; Terao, T.; Manabe, K.; Hirai, T.; Wu, C.-J.; Chuang, S.-C.; Kawano, S.; Murata, M.* “A Highly Conductive n-Type Coordination Complex with Thieno[3,2-b]thiophene Units: Facile Synthesis, Orientation, and Thermoelectric Properties” J. Am. Chem. Soc. 2022, 144, 18744-18749.
   7. Hsieh, C.-M.; Hsiao, H.-C.; Yamada, Y.; Wu, W.-R.; Jeng, U.-S.; Su, C.-J.;* Lin, Y.-S.; Murata, M.;* Chang, Y. J.;* Chuang, S.-C.* “Promoting the Efficiency and Stability of Nonfullerene Organic Photovoltaics by Incorporating Open-Cage [60]Fullerenes in the Nonfullerene Nanocrystallites” ACS Appl. Mater. Interfaces, 2022, 14, 39109.
   8. Nallapati, S.; Tseng, M.-F.; Chen, P.-L.; Chuang, S.-C.* “Phosphine-Mediated [4 + 3] Annulation of Diynoates and 2-Arylidene Indane-1,3-diones: Access of Indeno[1,2-b]oxepin-4-ylidenes and Beyond” Org. Lett. 2022, 24, 2993–2997.
   9. Hsiao, H.-C.; Chen, P.-L.; Chuang, S.-C.* “Crystal structure and fluorescence of 1-[8-phenyl-9-(phenylethynyl)-4H-benzo[def]carbazol-4-yl]-ethan-1-one” Acta Cryst. 2022. E78, 590-593.
   10. Hsieh, C.-M.; Chuang, M.-R.; Yamada, Y.; Su, C.-J.; Chang, Y. J.*; Murata, M.*; Jeng, U.-S.*; Chuang, S.-C.* “p-Tetrafluorophenylene divinylene-Bridged Nonfullerene Acceptors as Binary Components and Additives for High-efficiency Organic Solar Cells” ACS Appl. Mater. Interfaces, 2021, 13, 61473-61486.
   11. Sun, S.-Y.; Raju, S.; Vedarethinam, G.; Chen, P.-L.; Chuang, S.-C.* “TfOH-Promoted Classical Nazarov-type Cyclization of Benzofulvenes: Synthesis of Polycyclic 5H,10’H-spiro[benzo[k]phenanthridine-5,6′-dibenzopentalenes]” Org. Lett. 2021, 23, 6212–6216.
   12. Seo, J; Chen, C.-W.; Lee, W.; Jeon, J. E.; Chen, P.-L.; Chuang, S.-C.*; Joo, J. M.* Pd-Catalyzed C–H “Benzannulation of Functionalized Furans and Pyrroles with Alkynes” Synthesis 2021, 53, 3001-3010.

Song, J. Y.; Jang, J. H.; Chuang, S.-C.*; Joo, J. M.* “Palladium-catalyzed Aerobic Benzannulation of Pyrazoles with Alkynes” Bull. Kor. Chem. Soc. 2021, 42, 489-491.

Hsiao, H.-C.; Annamalai, P.; Jayakumar, J.; Sun, S.-Y.; Chuang, S.-C.* “Synthesis of Fluorescent 4-Azapyrenes by Palladium(II)-Catalyzed Dual C−H Bond Activation and Annulation” Adv. Synth. Catal. 2021, 363, 1695-1701.

Jillella, R.; Raju, S.; Hsiao, H.-C.; Hsu, D.-S.; Chuang, S.-C.* “Pd-Catalyzed Redox-Neutral C–N Coupling Reaction of Iminoquinones with Electron-Deficient Alkenes without External Oxidants: Access of Tertiary (E)-Enamines and Application to the Synthesis of Indoles and Quinolin-4-ones” Org. Lett. 2020, 22, 6252-6256.

Jayakumar, J.; Vedarethinam, G.; Hsiao, H.-C.; Sun, S.-Y.; Chuang, S.-C.* “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” Angew. Chem. Int. Ed. 2020, 59, 689-694.

Tseng, P.-Y.; Hsiao, H.-C.; Hsieh, C.-M.;Wu, A.-J.; Chuang, S.-C.* “Organic bulk heterojunction photovoltaics incorporating cyclopenteno[60]fullerene monoadducts as n-type materials display superior power conversion efficiency than with PC61BM” J. Chin. Chem. Soc. 2020, 67, 430 (Invited).

Annamalai, P.; Hsiao, H.-C.; Raju, S.; Fu, Y.-H.; Chen, P.-L.; Horng, J.-C.; Liu, Y.-H.; Chuang, S.-C.* “Synthesis, Isolation, and Characterization of Mono- and Bis-Norbornene Annulated Biarylamines Through Pseudo-Catellani Intermediates” Org. Lett. 2019, 21, 1182-1186.

Raju, S.; Hsiao, H.-C.; Thirupathi, S.; Chen, P.-L.; Chuang, S.-C.* “Palladium-Catalyzed Benzofulvenation of o-Arylanilines through C–H Bond Activation by Using Two Diarylacetylenes as an Implicit Benzofulvene” Adv. Synth. Catal. 2019, 361, 683-689.

Nallapati, S. B.; Chuang, S.-C.* “Phosphine-catalyzed Reactions with Unsaturated Carbonyl Compounds” Asian J. Org. Chem. 2018, 7, 1743-1757 (Invited review).

Chiou, M.-F.; Jayakumar, J.; Cheng, C.-H.; Chuang, S.-C.* “Impact of the Valence Charge of Transition Metals on the Cobalt- and Rhodium-Catalyzed Synthesis of Indenamines, Indenols, and Isoquinolinium Salts: A Catalytic Cycle Involving MIII/MV [M = Co, Rh] for [4+2] Annulation” J. Org. Chem. 2018, 83, 7814-7824.

Hsieh, C.-M.; Liao, Y.-S.; Lin, Y.-R.; Chen, C.-P.; Tsai, C.-M.; Diau, E. W.-G.; Chuang, S.-C.* “Low-Temperature, Simple and Efficient Preparation of Perovskite Solar Cells Using Lewis Bases Urea and Thiourea as Additives: Stimulating Large Grain Growth and Providing a PCE up to 18.8%” RSC Adv. 2018, 8, 19610-19615. (selected for the RSC Advances 10th Anniversary collection: Solar energy)

Annamalai, P.; Hsu, K.-C.; Raju, S.; Hsiao, H.-C.; Chou, C.-W.; Lin, G.-Y.; Hsieh, C.-M.; Chen, P.-L.; Liu, Y.-H.; Chuang, S.-C.* “Palladium (II)-catalyzed mono- and bis-alkenylation of N-acetyl-2-aminobiaryls through regioselective C–H bond activation” J. Org. Chem. 2018, 83, 3840-3856.

Upadhyay, N. S.; Thorat, V. H.; Sato, R.; Annamalai, P.; Chuang, S.-C.*; Cheng, C.-H.* “Synthesis of Isoquinolone via Rh-catalyzed C-H Activation of Substituted Benzamides as Air as the Sole Oxidant in Water” Green Chemistry, 2017, 19, 3219-3224.

Raju, S.; Annamalai, P.; Chen, P.-L.; Liu, Y.-H.; Chuang, S.-C.* “Palladium-Catalyzed C–H Bond Activation by Using Iminoquinone as a Directing Group and an Internal Oxidant or a Co-oxidant: Production of Dihydrophenanthridines, Phenanthridines, and Carbazoles” Org. Lett. 2017, 19, 4134-4137.

Raju, S.; Annamalai, P.; Chen, P.-L.; Liu, Y.-H.; Chuang, S.-C.* “Iptycenes with an acridinone motif developed through [4+2]cycloaddition of tethered naphthalene and iminoquinone via a radical reaction” Chem. Commun., 2017, 53, 6247-6250.

Raju, S.; Annamalai, P.; Chan, F.-W. Tseng, P.-Y.; Chen, P.-Y.; Kuo, T.-S.; Chuang, S.-C. “Palladium-Catalyzed Regio- and Stereoselective Hydrosulfonation of Propiolate Esters” Synthesis 2017, 49, 5007-5016.

Annamalai, P.; Chen, W.-Y.; Raju, S.; Hsu, K.-C.; Upadhyay, N. S.; Cheng, C.-H.*; Chuang, S.-C.* ” Palladium-Catalyzed Selective Aryl Ring C–H Activation of N-Acyl 2-Aminobiaryls: Efficient Access of Multiaryl Substituted Naphthalenes” Adv. Synth. Catal. 2016, 358, 3642–3648.

Chuang, S.-C.*; Sung, S.-P.; Deng, J.-C.; Chiou, M.-F.; Hsu, D.-S. “Multicomponent reactions of phosphines, enynedioates and benzylidene malononitriles generated highly substituted cyclopentenes through an unexpected phosphine alpha-addition-delta-evolvement of an anion pathway” Org. Biomol. Chem. 2016, 14, 2306–2317.

Wu, A.-J.; Tseng, P,-Y.; Hsu, W.-H.; Chuang, S.-C.* “Tricyclohexylphosphine-catalyzed Cycloaddition of Enynoates with [60]Fullerene and the Application of Cyclopentenofullerenes as n-Type Materials in Organic Photovoltaics” Org. Lett. 2016,18, 224–227.

Tai, H.-C.; Chavan, A. S.; Chuang, S.-C.* “Nucleophilic Conjugate 1,5-Addition of (E)-Hex-2-en-4-ynedioates towards Gilman Reagents: An Access toward b(g’)-Substituted Muconates” Synthesis 2015, 47, 2223–2232.

Deng, J.-C.; Chen, W.-Y.; Zhu, C.; Chuang, S.-C.* ” Multicomponent Reactions of Phosphines, Enynedioates and Cinnamaldimines Give γ-Lactams with a 1,3,5-Hexatriene Moiety for Facile 6p Electrocyclization: Access to Oxindoles, Isatins and Isoxazolinones” Adv. Synth. & Catal. 2015, 357, 1453–1462.

Chen, C.-P.*; Huang, C.-Y.; Chuang, S.-C.* “Highly Thermal Stable and Efficient Organic Photovoltaic Cells with Crosslinked Networks Appending Open-Cage Fullerenes as Additives” Adv. Funct. Mater., 2015, 15, 207–213 (Selected as a Frontispiece).

Deng, J.-C.; Chuang, S.-C.* “Multicomponent Reactions of Phosphines, Diynedioates and Aryl Aldehydes Generated Furans Appending Reactive Phosphorus Ylides through Cumulated Trienoates as Key Intermediates: A Phosphine a-Addition-d-Evolvement of an Anion Pathway” Org. Lett. 2014, 16, 5792–5795.

Jayakumar, J.; Parthasarathy, K.; Chen, Y.-H.; Lee, T.-H.; Chuang, S.-C.;* Cheng, C.-H.* “One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple C-H Activation and Annulation” Angew. Chem. Int. Ed. 2014, 53, 9889–9892.

Deng, J.-C.; Kuo, C.-W.; Chuang, S.-C.* “Nucleophilic Conjugate 1,3-Addition of Phosphines to Oligoynoates” Chem. Commun., 2014, 50, 10580–10583 (Selected as an Inside Back Cover).

Lin, Y.-W., Deng, J.-C., Hsieh, Y.-Z.; Chuang, S.-C.* “One-Pot Formation of Fluorescent g-Lactams Having an a-Phosphorus Ylide Moiety through Three-Component a(d’)-Michael Reaction of Phosphines with an Enyne and N-Tosyl Aldimines” Org. Biomol. Chem. 2014, 12, 162–170.

Lee, T.-H.; Jayakumar, J.; Cheng, C.-H.;* Chuang, S.-C.* “One Pot Synthesis of Bioactive Benzopyranones through Palladium-Catalyzed C−H Activation and CO Insertion to 2-Arylphenols” Chem. Commun., 2013, 49, 11797–11799.

Murata, Y.; Chuang, S.-C.; Tanabe, F.; Murata, M.; Komatsu, K. “Recognition of hydrogen isotopomers by an open-cage fullerene” Philosophical Transactions of the Royal Society, A: Mathematical, Physical & Engineering Sciences 2013, 371(1998), 20110629/1-20110629/6.

Tseng, B.-Y.; Chuang, S.-C.* “Chemo-, Regio- and Stereoselective Tricyclohexylphosphine-Catalyzed [3+2]Cycloaddition of Enynes with [60]Fullerene Initiated by 1,4-Michael Addition: Synthesis of Cyclopenteno[60]fullerenes and Their Electrochemical Properties” Adv. Synth. & Catal. 2013, 355, 2165–2171.

Rajeshkumar, V.; Lee, T.-H.; Chuang, S.-C.* “Palladium-Catalyzed Oxidative Insertion of Carbon Monoxide to N-Sulfonyl-2-aminobiaryls through C–H Bond Activation: Access to Bioactive Phenanthridinone Derivatives in One Pot” Org. Lett. 2013, 15, 1468–1471.

Chavan, A. S.; Deng, J.-C.; Chuang, S.-C.* “α(δ’)-Michael Addition of Alkyl amines to Dimethyl (E)-Hex-2-en-4-ynedioate: Synthesis of a,b-Dehydroamino Acid Derivatives” Molecules, 2013, 18, 2611–2622.

Rajeshkumar, V.; Chan, F.-W.; Chuang, S.-C.* “Palladium-Catalyzed and Hybrid Acids-Assisted Synthesis of [60]Fulleroazepines in One Pot Under Mild Conditions: Annulation of N-sulfonyl-2-aminobiaryls with [60]Fullerene through Sequential C–H Bond Activation, C–C and C–N Bond Formation” Adv. Synth. & Catal. 2012, 354, 2473–2483.

Deng, J.-C.; Chan, F.-W.; Kuo, C.-W.; Cheng, C.-A.; Huang, C.-Y. Chuang, S.-C.* “Assembly of Dimethyl Acetylenedicarboxylate and Phosphanes with Aldehydes Leading to g-Lactones Having a-Phosphorus Ylides as Wittig Reagents” Eur. J. Org. Chem. 2012, 5738–5747.

Rajeshkumar, V.; Chuang, S.-C.* “Evolution of Late Transition-Metal-Catalyzed Intermolecular Reductive Coupling Reaction of [60]Fullerene and N-sulfonylaldimines: Competing Formation of Hydrobenzylated [60]Fullerenes and 1,2-Dihydrofullerene” Eur. J. Org. Chem. 2012, 3795–3805.

Chuang, S.-C.;* Deng, J.-C.; Chan, F.-W.; Chen, S.-Y.; Huang, W.-J.; Lai, L.-H.; Rajeshkumar, V. “[3+2] Cycloaddition of Dialkyl (E)-Hex-2-en-4-ynedioates to [60]Fullerene by Phosphane-Promoted Tandem α(δ’)-Michael Additions” Eur. J. Org. Chem. 2012, 2606–2613.

Chen, C.-P.;* Lin, Y.-W.; Horng; J.-C.; Chuang, S.-C.* “Open-cage Fullerenes as n-Type Materials in Organic Photovoltaics: Relevance of Frontier Energy Levels, Carrier Mobility and Morphology of Different Sizable Open-cage Fullerenes with Power Conversion Efficiency in Devices” Adv. Energy Mat. 2011, 1, 776–780.

Chen, C.-P.;* Chen, Y.-D.; Chuang, S.-C.* “High-Performance and Highly-Durable Inverted Organic Photovoltaics Embedding Solution-Processable Vanadium Oxides as an Interfacial Hole-Transporting Layer” Adv. Mat. 2011, 11, 3859–3863.

Chuang, S.-C.;* Chiu, C.-W.; Chien, S.-C.; Chu, C.-W.; Chen, F.-C.* “1-(3-Methoxycarbonyl)propyl-2-selenyl-[6,6]-methanofullerene as a n-Type Material for Organic Solar Cells” Syn. Met. 2011, 161, 1624–1629.

Deng, J.-C.; Chuang, S.-C.* “Three-Component and Nonclassical Reaction of Phosphines with Enynes and Aldehydes: Formation of g-Lactones Featuring a-Phosphorus Ylides” Org. Lett. 2011, 13, 2248–2251.

Chuang, S.-C.*; RajeshKumar, V.; Cheng, C.-A.; Deng, J.-C.; Wang, G.-W.* “Annulation of Benzamides with [60]Fullerenes Through Palladium(II)-Catalyzed C-H Bond Activation” J. Org. Chem. 2011, 76, 1599–1604.

Chen, C.-P.; Luo, C.; Ting, C.; Chuang, S.-C.* “Organic Photovoltaics Incorporating Fulleroisoquinolinone as n-type Materials” Chem. Commun. 2011, 47, 1845–1847.

Su, H.-L.; Kao, W.-C.; Lee, C.-Y.; Chuang, S.-C.; Hsieh, Y.-Z.* “Separation of open-cage fullerenes using nonaqueous capillary electrophoresis” J. Chromatography A 2010, 1217, 4471–4475.

Chen, S.-Y.; Cheng, R.-L.; Tseng, C.-K.; Lin, Y.-S.; Lai,L.-H.; Venkatachalam, R. K.; Chen, Y.-C.; Cheng, C.-H.; Chuang, S.-C.* “Fullerene Derivatives Incorporating Phosphoramidous Ylide and Phosphoramidate: Synthesis and Property” J. Org. Chem. 2009, 74, 4866–4869.

Turro, N. J.; Marti, A. A.; Chen, J. Y.-C.; Jockusch, S.; Lawler, R. G.; Ruzzi, M.; Sartori, E.; Chuang, S.-C.; Komatsu, K.; Murata, Y. “Demonstration of a Chemical Transformation Inside a Fullerene. The Reversible Conversion of the Allotropes of H2@C60” J. Am. Chem. Soc. 2008, 130, 10506–10507.

Chin, K. K.; Chuang, S.-C.; Hernandez, B.; Selke, M.; Foote, C. S.; Garcia-Garibay, M. A. “Photophysical Properties of non-Homoconjugated 1,2-disubstituted, 1,2,3,4-tetrasubstituted, and 1,2,3,4,5,6-Hexasubstituted Fullerene Derivatives”, Photochemistry and Photobiological Science, 2008, 7, 49–55.

Chuang, S.-C.; Murata, Y.; Murata, M.; Komatsu, K. “An Orifice-Size Index for Open-Cage Fullerenes” J. Org. Chem. 2007, 72, 6447–6453.

Chuang, S.-C.; Murata, Y.; Murata, M.; Komatsu, K. “The Outside Knows the Difference Inside: Trapping Helium by Immediate Reduction of Orifice Size of an Open-Cage Fullerene and the Effect of Encapsulated Helium and Hydrogen upon NMR of the Proton Directly Attached to the Outside” Chem. Commun. 2007, 1751–1753.

Sander, M.; Jarrosson, T.; Chuang, S.-C.; Khan, S. I.; Rubin, Y. “Approaches to Open Fullerenes: Synthesis and Thermal Stability of cis-1 Bis(isobenzofuran) Diels-Alder Adducts of C60” J. Org. Chem. 2007, 72, 2724–2731.

Chuang, S.-C.; Jarrosson, T.; Sander, M.; James, S.; Rozumov, E.; Khan, S. I.; Rubin, Y. “Approaches to Open Fullerenes: Synthesis and Kinetic Stability of Diels-Alder Adducts of Substituted Isobenzofurans and C60” J. Org. Chem. 2007, 72, 2716–2723.

Chuang, S.-C.; Murata, Y.; Murata, M.; Mori, S.; Maeda, S.; Tanabe, F.; Komatsu, K. “Fine Tuning of the Orifice Size of an Open-Cage Fullerene by Placing Selenium in the Rim: Insertion/Release of Molecular Hydrogen”, Chem. Commun. 2007, 1278–1280.

Chin, K. K.; Chuang, S.-C.; Hernandez, B.; Selke, M.; Foote, C. S.; Garcia-Garibay, M. A. “Photophysical Properties of a 1,2,3,4,5,6-Hexasubstituted Fullerene Derivative”, J. Phy. Chem. A, 2006, 110, 13662–13666.

Chuang, S.-C.; Clemente, F.; Khan, S. I.; Houk, K. N.; Rubin, Y. “Approaches to Open Fullerenes: A 1,2,3,4,5,6-Hexaadduct of C60”, Org. Lett. 2006, 8, 4525–4528.

Chuang, S.-C.; Khan, Saeed I.; Rubin, Y. “Switch of Electronic Reactivity in Fullerene C60: Activation of Three trans-4 Positions via Temporary Saturation of the cis-1 Positions”, Org. Lett. 2006, 8, 6075–6078.

Chuang, S.-C. “Nano Sugery of C60” PhD dissertation, University of California, Los Angeles, 2005.

Qian, W.; Chuang, S.-C.; Amador, R. B.; Jarrosson, T.; Sander, M.; Pieniazek, S.; Khan, S. I.; Rubin, Y. “Synthesis of Stable Derivatives of C62: The First Nonclassical Fullerene Incorporating a Four-Membered Ring” J. Am. Chem. Soc., 2003, 125, 2066–2067.

Chuang, S.-C.; Islam, A.; Huang, C.-W.; Shih, H.-T.; Cheng, C.-H. “Novel Acid-Catalyzed Rearrangement of Methanofullerenes Bearing an -Ylidic Ester to Cyclopentanofullerenes: A Vinyl Cyclopropane-Type Ring Expansion” J. Org. Chem. 2003, 68, 3811–3816.

Chuang, S.-C.; Shih, H.-T.; Cheng, C.-H. “Interaction of Magnesium and Lithium Ions with [60]Fullerene Derivatives Bearing a Phosphorus Ylide Group” Fullerene Science and Technology 2001, 233–239.

Chuang, S.-C.; Lee, D.-D.; Santhosh, K. C.; Cheng, C.-H. “Fullerene Derivatives Bearing a Phosphite Ylide, Phosphonate, Phosphine Oxide, and Phosphonic Acid: Synthesis and Reactivities” J. Org. Chem. 1999, 64, 8868–8872.

Chuang, S.-C.; Santhosh, K. C.; Lin, C.-H.; Wang, S.-L.; Cheng, C.-H. “Synthesis and Chemistry of Fullerene Derivatives Bearing Phosphorus Substituents. Unusual Reaction of Phosphines with Electron-Deficient Acetylenes and C60” J. Org. Chem. 1999, 64, 6664–6669.