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Title: Tunable Crystallinity and Charge Transfer in Two-Dimensional G-Quadruplex Organic Frameworks

Abstract

Abstract DNA G‐quadruplex structures were recently discovered to provide reliable scaffolding for two‐dimensional organic frameworks due to the strong hydrogen‐bonding ability of guanine. Herein, 2,7‐diaryl pyrene building blocks with high HOMO energies and large optical gaps are incorporated into G‐quadruplex organic frameworks. The adjustable substitution on the aryl groups provides an opportunity to elucidate the framework formation mechanism; molecular non‐planarity is found to be beneficial for restricting interlayer slippage, and the framework crystallinity is highest when intermolecular interaction and non‐planarity strike a fine balance. When guanine‐functionalized pyrenes are co‐crystallized with naphthalene diimide, charge‐transfer (CT) complexes are obtained. The photophysical properties of the pyrene‐only and CT frameworks are characterized by UV/Vis and steady‐state and time‐resolved photoluminescence spectroscopies, and by EPR spectroscopy for the CT complex frameworks.

Authors:
 [1];  [2];  [1];  [1];  [1];  [3];  [1];  [2];  [1];  [4];  [5]; ORCiD logo [1]
+ Show Author Affiliations
  1. Department of Chemistry, Argonne-Northwestern Solar Energy Research (ANSER) Center, and Institute for Sustainability and Energy at Northwestern, Northwestern University, Evanston IL USA
  2. Department of Chemical & Biological Engineering, Northwestern University, Evanston IL USA
  3. Applied Physics Graduate Program, Northwestern University, Evanston IL USA
  4. Department of Chemistry, Argonne-Northwestern Solar Energy Research (ANSER) Center, and Institute for Sustainability and Energy at Northwestern, Northwestern University, Evanston IL USA; Department of Chemistry, King Abdulaziz University, Jeddah Saudi Arabia
  5. Department of Chemistry, Argonne-Northwestern Solar Energy Research (ANSER) Center, and Institute for Sustainability and Energy at Northwestern, Northwestern University, Evanston IL USA; Applied Physics Graduate Program, Northwestern University, Evanston IL USA
Publication Date:
Research Org.:
Northwestern Univ., Evanston, IL (United States); Univ. of Minnesota, Minneapolis, MN (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1537228
Alternate Identifier(s):
OSTI ID: 1424538
Grant/Contract Number:  
FG02-87ER13808; FG02-99ER14999; AC02-05CH11231; SC0008688
Resource Type:
Accepted Manuscript
Journal Name:
Angewandte Chemie (International Edition)
Additional Journal Information:
Journal Name: Angewandte Chemie (International Edition); Journal Volume: 57; Journal Issue: 15; Journal ID: ISSN 1433-7851
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
Chemistry

Citation Formats

Wu, Yi-Lin, Bobbitt, N. Scott, Logsdon, Jenna L., Powers-Riggs, Natalia E., Nelson, Jordan N., Liu, Xiaolong, Wang, Timothy C., Snurr, Randall Q., Hupp, Joseph T., Farha, Omar K., Hersam, Mark C., and Wasielewski, Michael R. Tunable Crystallinity and Charge Transfer in Two-Dimensional G-Quadruplex Organic Frameworks. United States: N. p., 2018. Web. doi:10.1002/anie.201800230.
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Wu, Yi-Lin, Bobbitt, N. Scott, Logsdon, Jenna L., Powers-Riggs, Natalia E., Nelson, Jordan N., Liu, Xiaolong, Wang, Timothy C., Snurr, Randall Q., Hupp, Joseph T., Farha, Omar K., Hersam, Mark C., & Wasielewski, Michael R. Tunable Crystallinity and Charge Transfer in Two-Dimensional G-Quadruplex Organic Frameworks. United States. https://doi.org/10.1002/anie.201800230
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Wu, Yi-Lin, Bobbitt, N. Scott, Logsdon, Jenna L., Powers-Riggs, Natalia E., Nelson, Jordan N., Liu, Xiaolong, Wang, Timothy C., Snurr, Randall Q., Hupp, Joseph T., Farha, Omar K., Hersam, Mark C., and Wasielewski, Michael R. Wed . "Tunable Crystallinity and Charge Transfer in Two-Dimensional G-Quadruplex Organic Frameworks". United States. https://doi.org/10.1002/anie.201800230. https://www.osti.gov/servlets/purl/1537228.
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@article{osti_1537228,
title = {Tunable Crystallinity and Charge Transfer in Two-Dimensional G-Quadruplex Organic Frameworks},
author = {Wu, Yi-Lin and Bobbitt, N. Scott and Logsdon, Jenna L. and Powers-Riggs, Natalia E. and Nelson, Jordan N. and Liu, Xiaolong and Wang, Timothy C. and Snurr, Randall Q. and Hupp, Joseph T. and Farha, Omar K. and Hersam, Mark C. and Wasielewski, Michael R.},
abstractNote = {Abstract DNA G‐quadruplex structures were recently discovered to provide reliable scaffolding for two‐dimensional organic frameworks due to the strong hydrogen‐bonding ability of guanine. Herein, 2,7‐diaryl pyrene building blocks with high HOMO energies and large optical gaps are incorporated into G‐quadruplex organic frameworks. The adjustable substitution on the aryl groups provides an opportunity to elucidate the framework formation mechanism; molecular non‐planarity is found to be beneficial for restricting interlayer slippage, and the framework crystallinity is highest when intermolecular interaction and non‐planarity strike a fine balance. When guanine‐functionalized pyrenes are co‐crystallized with naphthalene diimide, charge‐transfer (CT) complexes are obtained. The photophysical properties of the pyrene‐only and CT frameworks are characterized by UV/Vis and steady‐state and time‐resolved photoluminescence spectroscopies, and by EPR spectroscopy for the CT complex frameworks.},
doi = {10.1002/anie.201800230},
journal = {Angewandte Chemie (International Edition)},
number = 15,
volume = 57,
place = {United States},
year = {Wed Mar 07 00:00:00 EST 2018},
month = {Wed Mar 07 00:00:00 EST 2018}
}
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