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On the Search of a Silver Bullet for the Preparation of Bioinspired Molecular Electrets with Propensity to Transfer Holes at High Potentials

Derr, James Bennett and Rybicka-Jasińska, Katarzyna and Espinoza, Eli Misael and Morales, Maryann and Billones, Mimi Karen and Clark, John Anthony and Vullev, Valentine Ivanov (2021) On the Search of a Silver Bullet for the Preparation of Bioinspired Molecular Electrets with Propensity to Transfer Holes at High Potentials. Biomolecules, 11 (3). Art. No. 429. ISSN 2218-273X. PMCID PMC8001849. doi:10.3390/biom11030429.

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Biological structure-function relationships offer incomparable paradigms for charge-transfer (CT) science and its implementation in solar-energy engineering, organic electronics, and photonics. Electrets are systems with co-directionally oriented electric dopes with immense importance for CT science, and bioinspired molecular electrets are polyamides of anthranilic-acid derivatives with designs originating from natural biomolecular motifs. This publication focuses on the synthesis of molecular electrets with ether substituents. As important as ether electret residues are for transferring holes under relatively high potentials, the synthesis of their precursors presents formidable challenges. Each residue in the molecular electrets is introduced as its 2-nitrobenzoic acid (NBA) derivative. Hence, robust and scalable synthesis of ether derivatives of NBA is essential for making such hole-transfer molecular electrets. Purdie-Irvine alkylation, using silver oxide, produces with 90% yield the esters of the NBA building block for iso-butyl ether electrets. It warrants additional ester hydrolysis for obtaining the desired NBA precursor. Conversely, Williamson etherification selectively produces the same free-acid ether derivative in one-pot reaction, but a 40% yield. The high yields of Purdie-Irvine alkylation and the selectivity of the Williamson etherification provide important guidelines for synthesizing building blocks for bioinspired molecular electrets and a wide range of other complex ether conjugates.

Item Type:Article
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URLURL TypeDescription CentralArticle
Derr, James Bennett0000-0003-1309-9102
Espinoza, Eli Misael0000-0002-0134-2833
Morales, Maryann0000-0002-1778-8901
Clark, John Anthony0000-0001-5623-7291
Vullev, Valentine Ivanov0000-0002-3416-9686
Additional Information:© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// 4.0/). Received: 29 January 2021; Accepted: 7 March 2021; Published: 15 March 2021. Author Contributions: Conceptualization, V.I.V.; methodology, J.B.D.; validation, J.B.D. and K.R.-J.; formal analysis, J.B.D. and K.R.-J.; investigation, J.B.D., K.R.-J., E.M.E., M.M., M.K.B., and J.A.C.; data curation, J.B.D. and K.R.-J.; writing—original draft preparation, V.I.V., J.B.D., and K.R.-J.; writing—review and editing, V.I.V., J.B.D. and K.R.-J.; visualization, V.I.V., J.B.D. and K.R.-J.; supervision, V.I.V.; project administration, V.I.V.; funding acquisition, V.I.V. All authors have read and agreed to the published version of the manuscript. Funding: This research was funded by: (1) USA National Science Foundation, grant number CHE 1800602, and AGEP supplement supporting J.A.C.; and (2) American Chemical Society Petroleum Research Fund, grant number 60651-ND4. Institutional Review Board Statement: Not applicable. Informed Consent Statement: Not applicable. Data Availability Statement: Not applicable. Conflicts of Interest: The authors declare no conflict of interest.
Funding AgencyGrant Number
American Chemical Society Petroleum Research Fund60651-ND4
Subject Keywords:Purdie-Irvine alkylation; etherification; molecular electrets; dipoles
Issue or Number:3
PubMed Central ID:PMC8001849
Record Number:CaltechAUTHORS:20210414-130253964
Persistent URL:
Official Citation:Derr, J.B.; Rybicka-Jasińska, K.; Espinoza, E.M.; Morales, M.; Billones, M.K.; Clark, J.A.; Vullev, V.I. On the Search of a Silver Bullet for the Preparation of Bioinspired Molecular Electrets with Propensity to Transfer Holes at High Potentials. Biomolecules 2021, 11, 429.
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:108730
Deposited By: Tony Diaz
Deposited On:17 Apr 2021 00:07
Last Modified:17 Apr 2021 00:07

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