Syntheses of ZnO with Different Morphologies: Catalytic Activity toward Coumarin Synthesis via the Knoevenagel Condensation Reaction
Abstract
Heterogeneous catalysts are preferred in fine chemical industries due to their easy recovery and reusability. In this work, we report an easily scalable method of ZnO catalysts for coumarin synthesis. Nanocrystalline ZnO particles with diverse morphologies and crystallite sizes were prepared using different solvents. The change in morphology results in changes in band gaps, defects, basicity, and textural properties (surface areas, pore volumes, and pore sizes). The catalytic performances of the synthesized ZnO materials were tested using coumarin synthesis via the Knoevenagel condensation. The catalyst synthesized using methanol shows the highest activity and selectivity (conversion of 74%, selectivity of 94%) with a turnover number of 14.69. The increased activity of the ZnO synthesized in methanol is attributed to the combined effects of moderate basicity and relatively high textural properties of the sample.
- Publication Date:
- Research Org.:
- Univ. of Connecticut, Storrs, CT (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
- OSTI Identifier:
- 1598193
- Grant/Contract Number:
- FG02-86ER13622
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Inorganic Chemistry
- Additional Journal Information:
- Journal Volume: 58; Journal Issue: 9; Journal ID: ISSN 0020-1669
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; morphology; oxides; alcohols; catalysts; materials
Citation Formats
Shakil, Md. R., Meguerdichian, Andrew G., Tasnim, Habiba, Shirazi-Amin, Alireza, Seraji, Mohammad S., and Suib, Steven L. Syntheses of ZnO with Different Morphologies: Catalytic Activity toward Coumarin Synthesis via the Knoevenagel Condensation Reaction. United States: N. p., 2019.
Web. doi:10.1021/acs.inorgchem.9b00053.
Shakil, Md. R., Meguerdichian, Andrew G., Tasnim, Habiba, Shirazi-Amin, Alireza, Seraji, Mohammad S., & Suib, Steven L. Syntheses of ZnO with Different Morphologies: Catalytic Activity toward Coumarin Synthesis via the Knoevenagel Condensation Reaction. United States. https://doi.org/10.1021/acs.inorgchem.9b00053
Shakil, Md. R., Meguerdichian, Andrew G., Tasnim, Habiba, Shirazi-Amin, Alireza, Seraji, Mohammad S., and Suib, Steven L. Tue .
"Syntheses of ZnO with Different Morphologies: Catalytic Activity toward Coumarin Synthesis via the Knoevenagel Condensation Reaction". United States. https://doi.org/10.1021/acs.inorgchem.9b00053. https://www.osti.gov/servlets/purl/1598193.
@article{osti_1598193,
title = {Syntheses of ZnO with Different Morphologies: Catalytic Activity toward Coumarin Synthesis via the Knoevenagel Condensation Reaction},
author = {Shakil, Md. R. and Meguerdichian, Andrew G. and Tasnim, Habiba and Shirazi-Amin, Alireza and Seraji, Mohammad S. and Suib, Steven L.},
abstractNote = {Heterogeneous catalysts are preferred in fine chemical industries due to their easy recovery and reusability. In this work, we report an easily scalable method of ZnO catalysts for coumarin synthesis. Nanocrystalline ZnO particles with diverse morphologies and crystallite sizes were prepared using different solvents. The change in morphology results in changes in band gaps, defects, basicity, and textural properties (surface areas, pore volumes, and pore sizes). The catalytic performances of the synthesized ZnO materials were tested using coumarin synthesis via the Knoevenagel condensation. The catalyst synthesized using methanol shows the highest activity and selectivity (conversion of 74%, selectivity of 94%) with a turnover number of 14.69. The increased activity of the ZnO synthesized in methanol is attributed to the combined effects of moderate basicity and relatively high textural properties of the sample.},
doi = {10.1021/acs.inorgchem.9b00053},
journal = {Inorganic Chemistry},
number = 9,
volume = 58,
place = {United States},
year = {Tue Apr 09 00:00:00 EDT 2019},
month = {Tue Apr 09 00:00:00 EDT 2019}
}
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Works referenced in this record:
Discovery and synthesis of novel 3-phenylcoumarin derivatives as antidepressant agents
journal, April 2011
- Sashidhara, Koneni V.; Kumar, Abdhesh; Chatterjee, Manavi
- Bioorganic & Medicinal Chemistry Letters, Vol. 21, Issue 7
Synthesis, selective anti-Helicobacter pylori activity, and cytotoxicity of novel N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides
journal, August 2010
- Chimenti, Franco; Bizzarri, Bruna; Bolasco, Adriana
- Bioorganic & Medicinal Chemistry Letters, Vol. 20, Issue 16
Coumarins as Antioxidants
journal, September 2011
- Kostova, I.; Bhatia, S.; Grigorov, P.
- Current Medicinal Chemistry, Vol. 18, Issue 25
Coumarin: a potential nucleus for anti-inflammatory molecules
journal, November 2012
- Bansal, Yogita; Sethi, Purva; Bansal, Gulshan
- Medicinal Chemistry Research, Vol. 22, Issue 7
Studies on Coumarins and Coumarin-Related Compounds to Determine their Therapeutic Role in the Treatment of Cancer
journal, November 2004
- Lacy, Aoife
- Current Pharmaceutical Design, Vol. 10, Issue 30
Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs
journal, April 2014
- Sánchez-Recillas, Amanda; Navarrete-Vázquez, Gabriel; Hidalgo-Figueroa, Sergio
- European Journal of Medicinal Chemistry, Vol. 77
Coumarin−Purine Ribofuranoside Conjugates as New Agents against Hepatitis C Virus
journal, April 2011
- Hwu, Jih Ru; Lin, Shu-Yu; Tsay, Shwu-Chen
- Journal of Medicinal Chemistry, Vol. 54, Issue 7
Current Developments of Coumarin Compounds in Medicinal Chemistry
journal, April 2013
- Peng, Xin-Mei; L. V. Damu, Guri; He Zhou, Cheng-
- Current Pharmaceutical Design, Vol. 19, Issue 21
Recent Advances in the Synthesis of Coumarin Derivatives via Knoevenagel Condensation: A Review
journal, August 2014
- Vekariya, Rajesh H.; Patel, Hitesh D.
- Synthetic Communications, Vol. 44, Issue 19
Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin–resveratrol hybrids
journal, January 2006
- Vilar, Santiago; Quezada, Elías; Santana, Lourdes
- Bioorganic & Medicinal Chemistry Letters, Vol. 16, Issue 2
Synthesis of coumarins via Pechmann reaction catalyzed by 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable acidic ionic liquid
journal, January 2012
- Khaligh, Nader Ghaffari
- Catalysis Science & Technology, Vol. 2, Issue 8
Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts
journal, November 2017
- Bouasla, Souad; Amaro-Gahete, Juan; Esquivel, Dolores
- Molecules, Vol. 22, Issue 12
A practical one-pot synthesis of coumarins in aqueous sodium bicarbonate via intramolecular Wittig reaction at room temperature
journal, January 2014
- Belavagi, Ningaraddi S.; Deshapande, Narahari; Sunagar, Manjunath G.
- RSC Adv., Vol. 4, Issue 75
Facile One-Pot, Multicomponent Synthesis of Pyridines Under Microwave Irradiation
journal, March 2009
- Zhou, Jian-Feng; Song, Yuan-Zhi; Lv, Jin-Shun
- Synthetic Communications, Vol. 39, Issue 8
Synthesis, characterization and catalytic activity of melamine immobilized MCM-41 for condensation reactions
journal, July 2017
- Appaturi, Jimmy Nelson; Jothi Ramalingam, R.; Al-Lohedan, Hamad A.
- Journal of Porous Materials, Vol. 25, Issue 2
Highly efficient and recyclable basic ionic liquids supported on SBA-15 for the synthesis of substituted styrenes, carbinolamides, and naphthopyrans
journal, February 2017
- Sarmah, Bhaskar; Srivastava, Rajendra
- Molecular Catalysis, Vol. 427
Amino-grafted SBA-15 material as dual acid–base catalyst for the synthesis of coumarin derivatives
journal, May 2014
- Aider, Nadia; Smuszkiewicz, Agata; Pérez-Mayoral, Elena
- Catalysis Today, Vol. 227
Imidazolium chloride immobilized SBA-15 as a heterogenized organocatalyst for solvent free Knoevenagel condensation using microwave
journal, January 2012
- Parvin, Mst. Nargis; Jin, Hua; Ansari, Mohd. Bismillah
- Applied Catalysis A: General, Vol. 413-414
Preparation of acid-base bifunctional mesoporous KIT-6 (KIT: Korea Advanced Institute of Science and Technology) and its catalytic performance in Knoevenagel reaction
journal, May 2014
- Xu, Ling; Wang, Chunhua; Guan, Jingqi
- Journal of Solid State Chemistry, Vol. 213
The role of metallic modifiers of SBA-15 supports for propyl-amines on activity and selectivity in the Knoevenagel reactions
journal, April 2016
- Calvino-Casilda, Vanesa; Olejniczak, Magdalena; Martín-Aranda, Rosa María
- Microporous and Mesoporous Materials, Vol. 224
Control of amine functionality distribution in polyvinylamine/SBA-15 hybrid catalysts for Knoevenagel condensation
journal, April 2015
- Wach, Anna; Drozdek, Marek; Dudek, Barbara
- Catalysis Communications, Vol. 64
A facile method for synthesis of amine-functionalized mesoporous zirconia and its catalytic evaluation in Knoevenagel condensation
journal, June 2010
- Parida, K. M.; Mallick, Sujata; Sahoo, P. C.
- Applied Catalysis A: General, Vol. 381, Issue 1-2
Highly efficient green mesostructured urea functionalized on SBA-15 catalysts for selective synthesis of benzlidenemalononitrile
journal, January 2018
- Appaturi, Jimmy Nelson; Johan, Mohd. Rafie; Ramalingam, R. Jothi
- Microporous and Mesoporous Materials, Vol. 256
Synthesis of 3-(2-furylmethylene)-2,4-pentanedione using DL-Alanine functionalized MCM-41 catalyst via Knoevenagel condensation reaction
journal, April 2018
- Appaturi, Jimmy Nelson; Selvaraj, Manickam; Abdul Hamid, Sharifah Bee
- Microporous and Mesoporous Materials, Vol. 260
ZnO with Different Morphologies Synthesized by Solvothermal Methods for Enhanced Photocatalytic Activity
journal, May 2009
- Xu, Linping; Hu, Yan-Ling; Pelligra, Candice
- Chemistry of Materials, Vol. 21, Issue 13
A comprehensive review of ZnO materials and devices
journal, August 2005
- Özgür, Ü.; Alivov, Ya. I.; Liu, C.
- Journal of Applied Physics, Vol. 98, Issue 4
Zinc oxide nanostructures: growth, properties and applications
journal, June 2004
- Wang, Zhong Lin
- Journal of Physics: Condensed Matter, Vol. 16, Issue 25
ZnO nanoparticle as catalyst for efficient green one-pot synthesis of coumarins through Knoevenagel condensation
journal, September 2011
- Kumar, B. Vinay; Naik, Halehatty S. Bhojya; Girija, D.
- Journal of Chemical Sciences, Vol. 123, Issue 5, p. 615-621
Morphology-dependent photocatalytic activities of hierarchical microstructures of ZnO
journal, July 2011
- Kim, Dahye; Huh, Young-Duk
- Materials Letters, Vol. 65, Issue 14
Controllable synthesis of ZnO nanoflowers and their morphology-dependent photocatalytic activities
journal, September 2008
- Wang, Yuxin; Li, Xinyong; Wang, Ning
- Separation and Purification Technology, Vol. 62, Issue 3
Growth Mechanism of Different Morphologies of ZnO Crystals Prepared by Hydrothermal Method
journal, February 2011
- Wang, Hu; Xie, Juan; Yan, Kangping
- Journal of Materials Science & Technology, Vol. 27, Issue 2
Water Amount Dependence on Morphologies and Properties of ZnO nanostructures in Double-solvent System
journal, January 2014
- Yin, Jinzhou; Gao, Feng; Wei, Chengzhen
- Scientific Reports, Vol. 4, Issue 1
Synthesis of high surface area ZnO powder by continuous precipitation
journal, May 2012
- Boz, İsmail; Kaluza, Stefan; Boroğlu, Mehtap Şafak
- Materials Research Bulletin, Vol. 47, Issue 5
Variation of the specific surface area and porosity of zinc oxide prepared in various atmospheres
journal, April 1976
- Mikhail, Raouf Sh.; Guindy, Nabila M.; Ali, Ismail T.
- Journal of Applied Chemistry and Biotechnology, Vol. 26, Issue 4
Effect of variation of average pore size and specific surface area of ZnO electrode (WE) on efficiency of dye-sensitized solar cells
journal, October 2014
- Jadhav, Nitin A.; Singh, Pramod K.; Rhee, Hee Woo
- Nanoscale Research Letters, Vol. 9, Issue 1
Single-Doped and Multidoped Transition-Metal (Mn, Fe, Co, and Ni) ZnO and Their Electrocatalytic Activities for Oxygen Reduction Reaction
journal, April 2018
- Shakil, Md. R.; El-Sawy, Abdelhamid M.; Tasnim, Habiba
- Inorganic Chemistry, Vol. 57, Issue 16
Hydrothermal synthesis of one-dimensional ZnO nanostructures with different aspect ratios
journal, January 2004
- Cheng, Bin; Samulski, Edward T.
- Chemical Communications, Issue 8
Control of ZnO Morphology via a Simple Solution Route
journal, October 2002
- Zhang, Jun
- Chemistry of Materials, Vol. 14, Issue 10
Solvothermal Synthesis of ZnO with Various Aspect Ratios Using Organic Solvents
journal, September 2006
- Kunjara Na Ayudhya, Sirachaya; Tonto, Parawee; Mekasuwandumrong, Okorn
- Crystal Growth & Design, Vol. 6, Issue 11
Effect of different solvents on the structural and optical properties of zinc oxide thin films for optoelectronic applications
journal, January 2014
- Foo, K. L.; Kashif, M.; Hashim, U.
- Ceramics International, Vol. 40, Issue 1
Raman spectroscopy and magnetic properties of bulk ZnO:Co single crystal
journal, October 2006
- Millot, M.; Gonzalez, J.; Molina, I.
- Journal of Alloys and Compounds, Vol. 423, Issue 1-2
The effect of group-I elements on the structural and optical properties of ZnO nanoparticles
journal, March 2013
- Yousefi, Ramin; Zak, A. Khorsand; Jamali-Sheini, Farid
- Ceramics International, Vol. 39, Issue 2
Structural, elemental, optical and magnetic study of Fe doped ZnO and impurity phase formation
journal, April 2014
- Karamat, S.; Rawat, R. S.; Lee, P.
- Progress in Natural Science: Materials International, Vol. 24, Issue 2
Structural and spectroscopic characteristics of ZnO and ZnO:Er 3+ nanostructures
journal, September 2004
- Pradhan, A. K.; Zhang, Kai; Loutts, G. B.
- Journal of Physics: Condensed Matter, Vol. 16, Issue 39
Enhanced photocatalytic activity of Co doped ZnO nanodisks and nanorods prepared by a facile wet chemical method
journal, January 2014
- Kuriakose, Sini; Satpati, Biswarup; Mohapatra, Satyabrata
- Physical Chemistry Chemical Physics, Vol. 16, Issue 25
Electrical, dielectric, photoluminescence and magnetic properties of ZnO nanoparticles co-doped with Co and Cu
journal, January 2015
- Ashokkumar, M.; Muthukumaran, S.
- Journal of Magnetism and Magnetic Materials, Vol. 374
Structural, magnetic and optical studies of (Zn0.90Co0.05Ni0.05O) DMS
journal, October 2010
- Sebastian, K. C.; Chawda, Mukesh; Jonny, Linu
- Materials Letters, Vol. 64, Issue 20
Blue electroluminescence from Sb-ZnO/Cd-ZnO/Ga-ZnO heterojunction diode fabricated by dual ion beam sputtering
journal, January 2014
- Pandey, Sushil Kumar; Awasthi, Vishnu; Verma, Shruti
- Optics Express, Vol. 22, Issue 25
A simple and novel route for the preparation of ZnO nanorods
journal, April 2002
- Xu, Congkang; Xu, Guoding; Liu, Yingkai
- Solid State Communications, Vol. 122, Issue 3-4
Synthesis and Characterization of Poly(vinylpyrrolidone)-Modified Zinc Oxide Nanoparticles
journal, August 2000
- Guo, Lin; Yang, Shihe; Yang, Chunlei
- Chemistry of Materials, Vol. 12, Issue 8
Acidity/basicity of rare-earth oxides and their catalytic activity in oxidative coupling of methane to C2-hydrocarbons
journal, August 1991
- Choudhary, V.
- Journal of Catalysis, Vol. 130, Issue 2
Montmorillonite KSF as an Inorganic, Water Stable, and Reusable Catalyst for the Knoevenagel Synthesis of Coumarin-3-carboxylic Acids
journal, February 1999
- Bigi, Franca; Chesini, Luca; Maggi, Raimondo
- The Journal of Organic Chemistry, Vol. 64, Issue 3
A Straightforward Method for the Synthesis of Functionalized Trisubstituted Alkenes through Na 2 S/Al 2 O 3 Catalyzed Knoevenagel Condensation
journal, December 2007
- Heravi, Majid M.; Bakhtiari, Khadijeh; Taheri, Shima
- Journal of the Chinese Chemical Society, Vol. 54, Issue 6
Works referencing / citing this record:
Rapid, Efficient, and Green Synthesis of Coumarin Derivatives via Knoevenagel Condensation and Investigating Their Biological Effects
journal, August 2019
- Dinparast, Leila; Hemmati, Salar; Zengin, Gokhan
- ChemistrySelect, Vol. 4, Issue 31
Cellulose stabilized Fe 3 O 4 and carboxylate‐imidazole and Co‐based MOF growth as an exceptional catalyst for the Knoevenagel reaction
journal, January 2020
- Zare, Elham; Rafiee, Zahra
- Applied Organometallic Chemistry, Vol. 34, Issue 4
Synthesis, in-vitro antibacterial and anticancer screening of novel nicotinonitrile-coumarin hybrids utilizing piperazine citrate
journal, March 2020
- Sanad, Sherif M. H.; Mekky, Ahmed E. M.
- Synthetic Communications, Vol. 50, Issue 10
Synthesis, in-vitro antibacterial and anticancer screening of novel nicotinonitrile-coumarin hybrids utilizing piperazine citrate
text, January 2020
- Sanad, Sherif M. H.; Mekky, Ahmed E. M.
- Taylor & Francis