Abstract
Direct arylation polymerization (DArP) has emerged as an environmentally friendly, atom efficient method of synthesizing a variety of conjugated polymers. Here, we report a one-pot approach consisting of DArP followed by Boc deprotection to synthesize a functional, surface-active adenine-containing poly(alkylthiophene). Careful control over the polymerization temperature enables the one-pot polymerization and deprotection strategy for synthesis, with quantitative (>99%) Boc deprotection achieved in 24 h. This temperature-controlled synthesis method reduces extra purification and isolation steps, which makes the total synthesis more efficient and practical, and allows higher molecular weight polymer to be made. We quantify the hydrogen bonding ability of the resulting adenine-containing polythiophene, TAd-tT4h, by 1H NMR host-guest titration studies and analyze the results with the Benesi-Hildebrand model, yielding an association constant of 18.7 M-1 between alkylated thymine and TAd-tT4h. We demonstrate that TAd-tT4h robustly modifies the surface of cellulosic filter paper (CFP), and the modified cellulosic filter paper, CFP-TAd-tT4h, is an effective oil-water separatory filter with superhydrophobic properties (water contact angle (CA) ∼151°). The utility of hydrogen bonding interactions between adenine and cellulose highlights the importance of side-chain engineering for creating functional materials.
Original language | English |
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Pages (from-to) | 1012-1021 |
Number of pages | 10 |
Journal | ACS Applied Polymer Materials |
Volume | 3 |
Issue number | 2 |
DOIs | |
State | Published - Feb 12 2021 |
Funding
This material is based upon the work supported in part by the U.S. Department of Energy, Office of Nuclear Energy, Nuclear Energy Enabling Technologies (NEET) Program—Advanced Sensors and Instrumentation. Oak Ridge National Laboratory is managed by UT-Battelle, LLC, for the Department of Energy under contract DE-AC05-00OR22725.
Keywords
- direct arylation polymerization
- nucleobase
- oil-water separation
- superhydrophobic surface
- surface modification