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Title: Conjugated Macrocycles in Organic Electronics

Abstract

This Account describes a body of research on the design, synthesis, and application of a new class of electronic materials made from conjugated macrocycles. Our macrocyclic design takes into consideration the useful attributes of fullerenes and what properties make fullerenes efficient n-type materials. We identified four electronic and structural elements: (1) a three-dimensional shape; (2) a conjugated and delocalized π-space; (3) the presence of an interior and exterior to the π-surface; and (4) low-energy unoccupied molecular orbitals allowing them to accept electrons. The macrocyclic design incorporates some of these properties, including a three-dimensional shape, an interior/exterior to the π-surface, and low-lying LUMOs maintaining the n-type semiconducting behavior, yet we also install synthetic flexibility in our approach in order to tune the properties further. Each of the macrocycles comprises perylenediimide cores wound together with linkers. The perylenediimide building block endows each macrocycle with the ability to accept electrons, while the synthetic flexibility to install different linkers allows us to create macrocycles with different electronic properties and sizes. We have created three macrocycles that all absorb well into the visible range of the solar spectrum and possess different shapes and sizes. We then use these materials in an array of applications thatmore » take advantage of their ability to function as n-type semiconductors, absorb in the visible range of the solar spectrum, and possess intramolecular cavities. This Account will discuss our progress in incorporating these new macrocycles in organic solar cells, organic photodetectors, organic field effect transistors, and sensors. The macrocycles outperform acyclic controls in organic solar cells. We find the more rigid macrocyclic structure results in less intrinsic charges and lower dark current in organic photodetectors. Our macrocyclic-based photodetector has the highest detectivity of non-fullerene acceptors. The macrocycles also function as sensors and are able to recognize nuanced differences in analytes. Perylenediimide-based fused oligomers are efficient materials in both organic solar cells and field effect transistors. Here, we will use the oligomers to construct macrocycles for use in solar energy conversion. In addition, we will incorporate different electron-rich linkers in our cycles in an attempt to engineer the HOMO/LUMO gap further. Looking further into the future, we envision opportunities in applying these conjugated macrocycles as electronic host/guest materials, as concatenated electronic materials by threading the macrocycles with electroactive oligomers, and as a locus for catalysis that is driven by light and electric fields.« less

Authors:
 [1];  [1];  [1];  [1]; ORCiD logo [2];  [1];  [1]; ORCiD logo [3]
+ Show Author Affiliations
  1. Columbia University, New York, NY (United States)
  2. Shanghai Normal University (China)
  3. Columbia University, New York, NY (United States); Shanghai Normal University (China)
Publication Date:
Research Org.:
Columbia Univ., New York, NY (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)
OSTI Identifier:
2202973
Grant/Contract Number:  
SC0019440; FG02-01ER15264
Resource Type:
Accepted Manuscript
Journal Name:
Accounts of Chemical Research
Additional Journal Information:
Journal Volume: 52; Journal Issue: 4; Journal ID: ISSN 0001-4842
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Cavities; Macrocycles; Molecules; Oligomers; Solar cells

Citation Formats

Ball, Melissa, Zhang, Boyuan, Zhong, Yu, Fowler, Brandon, Xiao, Shengxiong, Ng, Fay, Steigerwald, Michael, and Nuckolls, Colin. Conjugated Macrocycles in Organic Electronics. United States: N. p., 2019. Web. doi:10.1021/acs.accounts.9b00017.
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Ball, Melissa, Zhang, Boyuan, Zhong, Yu, Fowler, Brandon, Xiao, Shengxiong, Ng, Fay, Steigerwald, Michael, & Nuckolls, Colin. Conjugated Macrocycles in Organic Electronics. United States. https://doi.org/10.1021/acs.accounts.9b00017
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Ball, Melissa, Zhang, Boyuan, Zhong, Yu, Fowler, Brandon, Xiao, Shengxiong, Ng, Fay, Steigerwald, Michael, and Nuckolls, Colin. Thu . "Conjugated Macrocycles in Organic Electronics". United States. https://doi.org/10.1021/acs.accounts.9b00017. https://www.osti.gov/servlets/purl/2202973.
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@article{osti_2202973,
title = {Conjugated Macrocycles in Organic Electronics},
author = {Ball, Melissa and Zhang, Boyuan and Zhong, Yu and Fowler, Brandon and Xiao, Shengxiong and Ng, Fay and Steigerwald, Michael and Nuckolls, Colin},
abstractNote = {This Account describes a body of research on the design, synthesis, and application of a new class of electronic materials made from conjugated macrocycles. Our macrocyclic design takes into consideration the useful attributes of fullerenes and what properties make fullerenes efficient n-type materials. We identified four electronic and structural elements: (1) a three-dimensional shape; (2) a conjugated and delocalized π-space; (3) the presence of an interior and exterior to the π-surface; and (4) low-energy unoccupied molecular orbitals allowing them to accept electrons. The macrocyclic design incorporates some of these properties, including a three-dimensional shape, an interior/exterior to the π-surface, and low-lying LUMOs maintaining the n-type semiconducting behavior, yet we also install synthetic flexibility in our approach in order to tune the properties further. Each of the macrocycles comprises perylenediimide cores wound together with linkers. The perylenediimide building block endows each macrocycle with the ability to accept electrons, while the synthetic flexibility to install different linkers allows us to create macrocycles with different electronic properties and sizes. We have created three macrocycles that all absorb well into the visible range of the solar spectrum and possess different shapes and sizes. We then use these materials in an array of applications that take advantage of their ability to function as n-type semiconductors, absorb in the visible range of the solar spectrum, and possess intramolecular cavities. This Account will discuss our progress in incorporating these new macrocycles in organic solar cells, organic photodetectors, organic field effect transistors, and sensors. The macrocycles outperform acyclic controls in organic solar cells. We find the more rigid macrocyclic structure results in less intrinsic charges and lower dark current in organic photodetectors. Our macrocyclic-based photodetector has the highest detectivity of non-fullerene acceptors. The macrocycles also function as sensors and are able to recognize nuanced differences in analytes. Perylenediimide-based fused oligomers are efficient materials in both organic solar cells and field effect transistors. Here, we will use the oligomers to construct macrocycles for use in solar energy conversion. In addition, we will incorporate different electron-rich linkers in our cycles in an attempt to engineer the HOMO/LUMO gap further. Looking further into the future, we envision opportunities in applying these conjugated macrocycles as electronic host/guest materials, as concatenated electronic materials by threading the macrocycles with electroactive oligomers, and as a locus for catalysis that is driven by light and electric fields.},
doi = {10.1021/acs.accounts.9b00017},
journal = {Accounts of Chemical Research},
number = 4,
volume = 52,
place = {United States},
year = {Thu Mar 14 00:00:00 EDT 2019},
month = {Thu Mar 14 00:00:00 EDT 2019}
}
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