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Title: Designing interchain and intrachain properties of conjugated polymers for latent optical information encoding

Abstract

Building molecular-design insights for controlling both the intrachain and the interchain properties of conjugated polymers (CPs) is essential to determine their characteristics and to optimize their performance in applications. However, most CP designs have focused on the conjugated main chain to control the intrachain properties, while the design of side chains is usually used to render CPs soluble, even though the side chains critically affect the interchain packing. Here, we present a straightforward and effective design strategy for modifying the optical and electrochemical properties of diketopyrrolopyrrole-based CPs by controlling both the intrachain and interchain properties in a single system. The synthesized polymers, P1, P2 and P3, show almost identical optical absorption spectra in solution, manifesting essentially the same intrachain properties of the three CPs having restricted effective conjugation along the main chain. However, the absorption spectra of CP films are gradually tuned by controlling the interchain packing through the side-chain design. Here, based on the tailored optical properties, we demonstrate the encoding of latent optical information utilizing the CPs as security inks on a silica substrate, which reveals and conceals hidden information upon the reversible aggregation/deaggregation of CPs.

Authors:
 [1];  [1];  [1];  [2];  [1];  [1];  [1]
  1. Univ. of Michigan, Ann Arbor, MI (United States)
  2. KonKuk Univ., Seoul (Republic of Korea)
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC), Washington, D.C. (United States). Center for Solar and Thermal Energy Conversion (CSTEC)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1370073
Grant/Contract Number:  
SC0000957
Resource Type:
Accepted Manuscript
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 6; Journal Issue: 12; Related Information: CSTEC partners with University of Michigan (lead); Kent State University; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Chung, Kyeongwoon, McAllister, Andrew, Bilby, David, Kim, Bong -Gi, Kwon, Min Sang, Kioupakis, Emmanouil, and Kim, Jinsang. Designing interchain and intrachain properties of conjugated polymers for latent optical information encoding. United States: N. p., 2015. Web. doi:10.1039/c5sc02403j.
Chung, Kyeongwoon, McAllister, Andrew, Bilby, David, Kim, Bong -Gi, Kwon, Min Sang, Kioupakis, Emmanouil, & Kim, Jinsang. Designing interchain and intrachain properties of conjugated polymers for latent optical information encoding. United States. doi:10.1039/c5sc02403j.
Chung, Kyeongwoon, McAllister, Andrew, Bilby, David, Kim, Bong -Gi, Kwon, Min Sang, Kioupakis, Emmanouil, and Kim, Jinsang. Thu . "Designing interchain and intrachain properties of conjugated polymers for latent optical information encoding". United States. doi:10.1039/c5sc02403j. https://www.osti.gov/servlets/purl/1370073.
@article{osti_1370073,
title = {Designing interchain and intrachain properties of conjugated polymers for latent optical information encoding},
author = {Chung, Kyeongwoon and McAllister, Andrew and Bilby, David and Kim, Bong -Gi and Kwon, Min Sang and Kioupakis, Emmanouil and Kim, Jinsang},
abstractNote = {Building molecular-design insights for controlling both the intrachain and the interchain properties of conjugated polymers (CPs) is essential to determine their characteristics and to optimize their performance in applications. However, most CP designs have focused on the conjugated main chain to control the intrachain properties, while the design of side chains is usually used to render CPs soluble, even though the side chains critically affect the interchain packing. Here, we present a straightforward and effective design strategy for modifying the optical and electrochemical properties of diketopyrrolopyrrole-based CPs by controlling both the intrachain and interchain properties in a single system. The synthesized polymers, P1, P2 and P3, show almost identical optical absorption spectra in solution, manifesting essentially the same intrachain properties of the three CPs having restricted effective conjugation along the main chain. However, the absorption spectra of CP films are gradually tuned by controlling the interchain packing through the side-chain design. Here, based on the tailored optical properties, we demonstrate the encoding of latent optical information utilizing the CPs as security inks on a silica substrate, which reveals and conceals hidden information upon the reversible aggregation/deaggregation of CPs.},
doi = {10.1039/c5sc02403j},
journal = {Chemical Science},
number = 12,
volume = 6,
place = {United States},
year = {2015},
month = {9}
}

Journal Article:
Free Publicly Available Full Text
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Cited by: 8 works
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Figures / Tables:

Fig. 1 Fig. 1: Chemical structures of the designed CPs: P1, P2 and P3. All three polymers have a phenyl linker between the electron-donating and electron-withdrawing building blocks to control the intrachain properties of CPs. Side chains with different bulkiness and direction are implemented to control the interchain interactions between CP chains.

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    Works referencing / citing this record:

    Ground and Excited States of Bis‐4‐Methoxybenzyl‐Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies
    journal, June 2019

    • Murphy, Alanna S.; Killalea, C. Elizabeth; Humphreys, Joshua
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      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.