Formation Mechanisms and Defect Engineering of Imine-Based Porous Organic Cages

Zhu, Guanghui; Liu, Yang; Flores, Luis; Lee, Zachary R.; Jones, Christopher W.; Dixon, David A.; Sholl, David S.; Lively, Ryan P.

doi:10.1021/acs.chemmater.7b04323

Title: Formation Mechanisms and Defect Engineering of Imine-Based Porous Organic Cages

Journal Article · Mon Dec 11 00:00:00 EST 2017 · Chemistry of Materials

DOI:https://doi.org/10.1021/acs.chemmater.7b04323· OSTI ID:1470285

Zhu, Guanghui ^[1]; Liu, Yang ^[1]; Flores, Luis ^[2]; Lee, Zachary R. ^[2]; Jones, Christopher W. ^[1];

^[2];

^[1];

^[1]

Georgia Inst. of Technology, Atlanta, GA (United States)
Univ. of Alabama, Tuscaloosa, AL (United States)

The syntheses of porous organic cages (POCs) represent an important synthetic puzzle in dynamic covalent chemistry based self-sorting. Improved understanding of the formation mechanisms of POCs can lead to control and rational design of cages with desired functionality. Herein, we explore the formation mechanisms of imine-based POCs using time-resolved electrospray mass spectrometry, and electronic structure calculations at the density functional theory and correlated molecular orbital theory levels. We find that the synthesis of the [4+6] cycloimine cage CC3-R and the [2+3] cycloimine cage CC-pentane both proceed through similar intermediates via a series of consecutive reactions. The proposed reaction mechanisms are supported by electronic structure calculations. Based on our observations from both experiments and calculations, we propose a comprehensive method for designing and predicting new POC species. In addition, the observation of stable incomplete cages during CC3-R synthesis inspired us to design intentionally defective cages. These “missing-linker” type molecular defects are installed into CC3-R via non-solvent induced crystallization. The defective CC3-R materials are found to have enhanced CO2 interaction and improved CO₂ uptake capacity due to the additional functional groups present within the CC3 crystals.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Understanding and Control of Acid Gas-induced Evolution of Materials for Energy (UNCAGE-ME)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0012577

OSTI ID:: 1470285

Journal Information:: Chemistry of Materials, Vol. 30, Issue 1; Related Information: UNCAGE-ME partners with Georgia Institute of Technology (lead); Lehigh University; Oak Ridge National Laboratory; University of Alabama; University of Florida; University of Wisconsin; Washington University in St. Louis; ISSN 0897-4756

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 34 works

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