Molecular modification effects on the electrochromic and photochromic properties of diarylethene with intramolecular isomerization behavior

Diarylethene (DAE) is one of the most widely used functional units for electrochromic or photochromic materials. To better understand the molecular modification effects on the electrochromic and photochromic properties of DAE, two modification strategies, substitution with functional groups or heter...

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Veröffentlicht in:The Journal of chemical physics 2023-03, Vol.158 (11), p.114701-114701
Hauptverfasser: Huang, Luyan, Zhao, Yongze, Huang, Zehua, Tang, Xinyuan, Liang, Xuefeng, Zhang, Lisheng, He, Yan, Li, Huifang
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container_end_page 114701
container_issue 11
container_start_page 114701
container_title The Journal of chemical physics
container_volume 158
creator Huang, Luyan
Zhao, Yongze
Huang, Zehua
Tang, Xinyuan
Liang, Xuefeng
Zhang, Lisheng
He, Yan
Li, Huifang
description Diarylethene (DAE) is one of the most widely used functional units for electrochromic or photochromic materials. To better understand the molecular modification effects on the electrochromic and photochromic properties of DAE, two modification strategies, substitution with functional groups or heteroatoms, were investigated theoretically by density functional theory calculations. It is found that red-shifted absorption spectra caused by a decreased highest occupied molecular orbital–lowest unoccupied molecular orbital energy gap and S0 → S1 transition energy during the ring-closing reaction become more significant by adding different functional substituents. In addition, for two isomers, the energy gap and S0 → S1 transition energy decreased by heteroatom substitution of S atoms with O or NH, while they increased by replacing two S atoms with CH2. For intramolecular isomerization, one-electron excitation is the most effective way to trigger the closed-ring (O → C) reaction, while the open-ring (C → O) reaction occurs most readily in the presence of one-electron reduction. Moreover, it is confirmed that substitution with strong electron donating groups (–OCH3/–NH2) or with one O/two CH2 heteroatoms leads to a more favorable closed-ring (O → C) reaction. Functionalized with strong electron-withdrawing groups (–NO2 and –COOH) or one/two NH heteroatom substitutions, the open-ring (C → O) reaction is easier. Our results confirmed that the photochromic and electrochromic properties of DAE can be tuned effectively by molecular modifications, which provides theoretical guidance for the design of new DAE-based photochromic/electrochromic materials.
doi_str_mv 10.1063/5.0141644
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To better understand the molecular modification effects on the electrochromic and photochromic properties of DAE, two modification strategies, substitution with functional groups or heteroatoms, were investigated theoretically by density functional theory calculations. It is found that red-shifted absorption spectra caused by a decreased highest occupied molecular orbital–lowest unoccupied molecular orbital energy gap and S0 → S1 transition energy during the ring-closing reaction become more significant by adding different functional substituents. In addition, for two isomers, the energy gap and S0 → S1 transition energy decreased by heteroatom substitution of S atoms with O or NH, while they increased by replacing two S atoms with CH2. For intramolecular isomerization, one-electron excitation is the most effective way to trigger the closed-ring (O → C) reaction, while the open-ring (C → O) reaction occurs most readily in the presence of one-electron reduction. Moreover, it is confirmed that substitution with strong electron donating groups (–OCH3/–NH2) or with one O/two CH2 heteroatoms leads to a more favorable closed-ring (O → C) reaction. Functionalized with strong electron-withdrawing groups (–NO2 and –COOH) or one/two NH heteroatom substitutions, the open-ring (C → O) reaction is easier. 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To better understand the molecular modification effects on the electrochromic and photochromic properties of DAE, two modification strategies, substitution with functional groups or heteroatoms, were investigated theoretically by density functional theory calculations. It is found that red-shifted absorption spectra caused by a decreased highest occupied molecular orbital–lowest unoccupied molecular orbital energy gap and S0 → S1 transition energy during the ring-closing reaction become more significant by adding different functional substituents. In addition, for two isomers, the energy gap and S0 → S1 transition energy decreased by heteroatom substitution of S atoms with O or NH, while they increased by replacing two S atoms with CH2. For intramolecular isomerization, one-electron excitation is the most effective way to trigger the closed-ring (O → C) reaction, while the open-ring (C → O) reaction occurs most readily in the presence of one-electron reduction. Moreover, it is confirmed that substitution with strong electron donating groups (–OCH3/–NH2) or with one O/two CH2 heteroatoms leads to a more favorable closed-ring (O → C) reaction. Functionalized with strong electron-withdrawing groups (–NO2 and –COOH) or one/two NH heteroatom substitutions, the open-ring (C → O) reaction is easier. Our results confirmed that the photochromic and electrochromic properties of DAE can be tuned effectively by molecular modifications, which provides theoretical guidance for the design of new DAE-based photochromic/electrochromic materials.</description><subject>Absorption spectra</subject><subject>Density functional theory</subject><subject>Electrochromism</subject><subject>Energy gap</subject><subject>Functional groups</subject><subject>Isomerization</subject><subject>Molecular orbitals</subject><subject>Nitrogen dioxide</subject><subject>Photochromism</subject><subject>Substitution reactions</subject><issn>0021-9606</issn><issn>1089-7690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp90V9L3TAUAPAgit6pD36BEfBlDupO2jRtHkXmHCh78b2k6QmNtE2XpIr7CvvSZt7rFYT5lEP4nT-cQ8gJg3MGovhWngPjTHC-Q1YMaplVQsIuWQHkLJMCxAH5FMI9ALAq5_vkoBCS1zXIFfl76wbUy6A8HV1njdUqWjdRNAZ1DDSFsUeKCUXvdO_daDVVU0fn3sXtx-zdjD5aTBmGdlb5pwFT4oT00cae2il6NW5b2eBG9PbPuleLvXqwzh-RPaOGgMeb95DcXX2_u7zObn79-Hl5cZNpzuqY5UWhlRLcFEawVrSdULxsRck0Vlh3AkEJWecS84RUV3HUgiNvq5bzxItD8mVdNg39e8EQm9EGjcOgJnRLaPJKApR5ISHR03f03i1-SsMlVQspOYgyqbO10t6F4NE0s7djWkHDoPl3oKZsNgdK9vOm4tKO2G3l60US-LoGQdv4sp8Pq_0XPzj_Bpu5M8UzjKKq3g</recordid><startdate>20230321</startdate><enddate>20230321</enddate><creator>Huang, Luyan</creator><creator>Zhao, Yongze</creator><creator>Huang, Zehua</creator><creator>Tang, Xinyuan</creator><creator>Liang, Xuefeng</creator><creator>Zhang, Lisheng</creator><creator>He, Yan</creator><creator>Li, Huifang</creator><general>American Institute of Physics</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>8FD</scope><scope>H8D</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7438-6116</orcidid><orcidid>https://orcid.org/0000-0001-6739-7151</orcidid><orcidid>https://orcid.org/0000-0001-7640-8377</orcidid><orcidid>https://orcid.org/0000-0002-6993-7198</orcidid><orcidid>https://orcid.org/0000-0003-1261-4491</orcidid><orcidid>https://orcid.org/0000-0002-5796-7285</orcidid><orcidid>https://orcid.org/0000-0002-1203-027X</orcidid><orcidid>https://orcid.org/0000-0003-4265-9594</orcidid></search><sort><creationdate>20230321</creationdate><title>Molecular modification effects on the electrochromic and photochromic properties of diarylethene with intramolecular isomerization behavior</title><author>Huang, Luyan ; Zhao, Yongze ; Huang, Zehua ; Tang, Xinyuan ; Liang, Xuefeng ; Zhang, Lisheng ; He, Yan ; Li, Huifang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c418t-233caa64f3f61b6bd6a45b651ce7e8d6e0a69829e2a64ad74ec64e4b7b44b6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Absorption spectra</topic><topic>Density functional theory</topic><topic>Electrochromism</topic><topic>Energy gap</topic><topic>Functional groups</topic><topic>Isomerization</topic><topic>Molecular orbitals</topic><topic>Nitrogen dioxide</topic><topic>Photochromism</topic><topic>Substitution reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Luyan</creatorcontrib><creatorcontrib>Zhao, Yongze</creatorcontrib><creatorcontrib>Huang, Zehua</creatorcontrib><creatorcontrib>Tang, Xinyuan</creatorcontrib><creatorcontrib>Liang, Xuefeng</creatorcontrib><creatorcontrib>Zhang, Lisheng</creatorcontrib><creatorcontrib>He, Yan</creatorcontrib><creatorcontrib>Li, Huifang</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Technology Research Database</collection><collection>Aerospace Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>The Journal of chemical physics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huang, Luyan</au><au>Zhao, Yongze</au><au>Huang, Zehua</au><au>Tang, Xinyuan</au><au>Liang, Xuefeng</au><au>Zhang, Lisheng</au><au>He, Yan</au><au>Li, Huifang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Molecular modification effects on the electrochromic and photochromic properties of diarylethene with intramolecular isomerization behavior</atitle><jtitle>The Journal of chemical physics</jtitle><addtitle>J Chem Phys</addtitle><date>2023-03-21</date><risdate>2023</risdate><volume>158</volume><issue>11</issue><spage>114701</spage><epage>114701</epage><pages>114701-114701</pages><issn>0021-9606</issn><eissn>1089-7690</eissn><coden>JCPSA6</coden><abstract>Diarylethene (DAE) is one of the most widely used functional units for electrochromic or photochromic materials. To better understand the molecular modification effects on the electrochromic and photochromic properties of DAE, two modification strategies, substitution with functional groups or heteroatoms, were investigated theoretically by density functional theory calculations. It is found that red-shifted absorption spectra caused by a decreased highest occupied molecular orbital–lowest unoccupied molecular orbital energy gap and S0 → S1 transition energy during the ring-closing reaction become more significant by adding different functional substituents. In addition, for two isomers, the energy gap and S0 → S1 transition energy decreased by heteroatom substitution of S atoms with O or NH, while they increased by replacing two S atoms with CH2. For intramolecular isomerization, one-electron excitation is the most effective way to trigger the closed-ring (O → C) reaction, while the open-ring (C → O) reaction occurs most readily in the presence of one-electron reduction. Moreover, it is confirmed that substitution with strong electron donating groups (–OCH3/–NH2) or with one O/two CH2 heteroatoms leads to a more favorable closed-ring (O → C) reaction. Functionalized with strong electron-withdrawing groups (–NO2 and –COOH) or one/two NH heteroatom substitutions, the open-ring (C → O) reaction is easier. 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subjects Absorption spectra
Density functional theory
Electrochromism
Energy gap
Functional groups
Isomerization
Molecular orbitals
Nitrogen dioxide
Photochromism
Substitution reactions
title Molecular modification effects on the electrochromic and photochromic properties of diarylethene with intramolecular isomerization behavior
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