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Microcrystal Electron Diffraction Elucidates Water-Specific Polymorphism-Induced Emission Enhancement of Bis-arylacylhydrazone

Cho, Hye Jin and Kim, Kyung-su and Kim, Hyunwoo and Kim, Taewoo and Malyutin, Andrey G. and Rees, Douglas C. and Yoo, Byung-Kuk and Song, Changsik (2021) Microcrystal Electron Diffraction Elucidates Water-Specific Polymorphism-Induced Emission Enhancement of Bis-arylacylhydrazone. ACS Applied Materials & Interfaces, 13 (6). pp. 7546-7555. ISSN 1944-8244. https://resolver.caltech.edu/CaltechAUTHORS:20210208-144010742

[img] PDF (Absorption and emission spectra of BAHs; DSL data of BAH-1 in a DMSO/water cosolvent system; optical images of BAH-1 on a silicon wafer; structure and information of crystals of BAH-1; simulated FTIR and absorption spectra of BAH-1; Hirshfeld surface ...) - Supplemental Material
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[img] Crystallographic Info File (CIF) (Crystallographic data of BAH-1-MeOH) - Supplemental Material
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[img] Crystallographic Info File (CIF) (Crystallographic data of BAH-1-H₂O) - Supplemental Material
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Abstract

Aggregation-induced emission (AIE) phenomena have gained intense interest over the last decades because of its importance in solid-state emission. However, the elucidation of a working mechanism is difficult owing to the limited characterization methods on solid-state molecules, further complicated if dynamic structural changes occur. Here, a series of bis-arylacylhydrazones (BAHs) were synthesized, for which their AIE properties are only turned on by the reversible adsorption of water molecules. We used microcrystal electron diffraction (MicroED) to determine the molecular structures of two BAHs directly from bulk powders (without attempting to grow crystals) prepared in the absence or presence of water adsorption. This study reveals the unambiguous characterization of the dependence of crystal packing on the specific cocrystallization with hydrates. The structural analysis demonstrates that water molecules form strong hydrogen bonds with three neighboring BAH-1, resulting in the almost complete planarization and restriction of the intramolecular rotation of the molecule. MicroED plays an important role in providing a decisive clue for the reversible polymorphism changes induced by the adsorption of water molecules, regulating emissive properties.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acsami.0c21248DOIArticle
ORCID:
AuthorORCID
Malyutin, Andrey G.0000-0003-1716-5437
Rees, Douglas C.0000-0003-4073-1185
Yoo, Byung-Kuk0000-0002-2610-6685
Song, Changsik0000-0003-4754-1843
Additional Information:© 2021 American Chemical Society. Received: November 30, 2020; Accepted: January 24, 2021; Published: February 5, 2021. This work was supported by the Nano Material Development Program (2012M3A7B4049677) and the Basic Science Research Program (2019R1A2C1004256) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science and ICT, Republic of Korea. This research was also supported partially by the Howard Hughes Medical Institute. B.-K.Y. thanks Lawrence M. Henling and Chih-Te Zee for crystallographic assistance as well as Dr. Oh-Hoon Kwon (during his sabbatical stay at Caltech) and Dr. Jens Kaiser for fruitful discussions. C. S. thanks Prof. Jin Yong Lee, Jong Hyeon Lim, and Hyun Dong Kim for their assistance in computational calculations. Author Contributions. H.J.C. and K.S.K. contributed equally to this study. The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
National Research Foundation of Korea2012M3A7B4049677
National Research Foundation of Korea2019R1A2C1004256
Howard Hughes Medical Institute (HHMI)UNSPECIFIED
Subject Keywords:MicroED; AIE; hydrazone; polymorphism; CIEE
Issue or Number:6
Record Number:CaltechAUTHORS:20210208-144010742
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210208-144010742
Official Citation:Microcrystal Electron Diffraction Elucidates Water-Specific Polymorphism-Induced Emission Enhancement of Bis-arylacylhydrazone. Hye Jin Cho, Kyung-su Kim, Hyunwoo Kim, Taewoo Kim, Andrey G. Malyutin, Douglas C. Rees, Byung-Kuk Yoo, and Changsik Song. ACS Applied Materials & Interfaces 2021 13 (6), 7546-7555 DOI: 10.1021/acsami.0c21248
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:107957
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:09 Feb 2021 15:33
Last Modified:18 Feb 2021 17:44

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