Computational Chemistry-Guided Design of Selective Chemoresponsive Liquid Crystals Using Pyridine and Pyrimidine Functional Groups

Yu, Huaizhe; Szilvási, Tibor; Rai, Prabin; Twieg, Robert J.; Mavrikakis, Manos; Abbott, Nicholas L.

doi:10.1002/adfm.201703581

Title: Computational Chemistry-Guided Design of Selective Chemoresponsive Liquid Crystals Using Pyridine and Pyrimidine Functional Groups

Journal Article · 19 January 2018 · Advanced Functional Materials

DOI: https://doi.org/10.1002/adfm.201703581 · OSTI ID:1543457

Yu, Huaizhe ^[1];

^[1]; Rai, Prabin ^[2];

^[2];

^[1];

^[1]

Univ. of Wisconsin, Madison, WI (United States)
Kent State Univ., Kent, OH (United States)

Abstract Computational chemistry‐guided designs of chemoresponsive liquid crystals (LCs) with pyridine or pyrimidine groups that bind to metal‐cation‐functionalized surfaces to provide improved selective responses to targeted vapor species (dimethylmethylphosphonate (DMMP)) over nontargeted species (water) are reported. The LC designs against experiments are tested by synthesizing 4‐(4‐pentyl‐phenyl)‐pyridine and 5‐(4‐pentyl‐phenyl)‐pyrimidine and quantifying LC responses to DMMP and water. Consistent with the computations, pyridine‐containing LCs bind to metal‐cation‐functionalized surfaces too strongly to permit a response to either DMMP or water whereas pyrimidine‐containing LCs undergo a surface‐driven orientational transition in response to DMMP without interference from water. The computation predictions are not strongly dependent on assumptions regarding the degree of coordination of the metal ions but are limited in their ability to predict LC responses when using cations with mostly empty d orbitals. Overall, this work identifies a promising new class of chemoresponsive LCs based on pyrimidine that exhibits enhanced tolerance to water, a result that is important because water is a ubiquitous and particularly challenging chemical interferent in chemical sensing strategies based on LCs. The work also provides further evidence of the transformative utility of computational chemistry methods to design LC materials that exhibit selective orientational responses in specific chemical environments.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC); Univ. of California, Oakland, CA (United States); Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: AC02-05CH11231; AC02-06CH11357; DE‐AC02‐06CH11357; DE‐AC02‐05CH11231

OSTI ID:: 1543457

Alternate ID(s):: OSTI ID: 1417497

Journal Information:: Advanced Functional Materials, Vol. 28, Issue 13; ISSN 1616-301X

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 25 works

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