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Theoretical Study on Photoisomerization Effect with a Reversible Nonlinear Optical Switch for Dithiazolylarylene
DFT and TDDFT methods have been performed to investigate the photoisomerization effect for dithiazolylarylene on solution. The weak S···N interaction and CH···N hydrogen bond restrain the rotation of the side-chain thiazolyl ring in open-isomer 1a, the higher stability of which prefers to show a hig...
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Published in: | The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2012-06, Vol.116 (22), p.5392-5397 |
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creator | Song, Ping Gao, Ai-Hua Zhou, Pan-Wang Chu, Tian-Shu |
description | DFT and TDDFT methods have been performed to investigate the photoisomerization effect for dithiazolylarylene on solution. The weak S···N interaction and CH···N hydrogen bond restrain the rotation of the side-chain thiazolyl ring in open-isomer 1a, the higher stability of which prefers to show a high quantum yield of photoisomerization. The calculated UV–Vis spectrum at around 320 nm for open-isomer 1a is bathochromically shifted to 647 nm for closed-isomer 1b, in excellent agreement with the experimental photochromic phenomenon. The electron transition in ECD (electron circular dichroism) spectra for closed-isomer 1b with two chiral carbon atoms is dominated by ICT (intramolecular charge transition) and LE (local excitation) corresponding to one positive (440 nm) and one negative Cotton effect (650 nm), respectively, where the two chiral carbon atoms play a slight role in these transitions. The PES in the S1 and S0 states, respectively, indicates that the cyclization reaction from open-isomer 1a to closed-isomer 1b is allowed in the photoexcited state with high-conversion quantum efficiency, while it is forbidden in the thermodynamic process. In addition, the second-order nonlinear optical response for closed-isomer 1b is nearly six times larger than that for open-isomer 1a. It is also confirmed that the photoirradiation evokes the photoisomerization character to show dramatic difference in the second-order NLO response, which can be applied to designing photochromic materials and reversible NLO switches. |
doi_str_mv | 10.1021/jp302535m |
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The weak S···N interaction and CH···N hydrogen bond restrain the rotation of the side-chain thiazolyl ring in open-isomer 1a, the higher stability of which prefers to show a high quantum yield of photoisomerization. The calculated UV–Vis spectrum at around 320 nm for open-isomer 1a is bathochromically shifted to 647 nm for closed-isomer 1b, in excellent agreement with the experimental photochromic phenomenon. The electron transition in ECD (electron circular dichroism) spectra for closed-isomer 1b with two chiral carbon atoms is dominated by ICT (intramolecular charge transition) and LE (local excitation) corresponding to one positive (440 nm) and one negative Cotton effect (650 nm), respectively, where the two chiral carbon atoms play a slight role in these transitions. The PES in the S1 and S0 states, respectively, indicates that the cyclization reaction from open-isomer 1a to closed-isomer 1b is allowed in the photoexcited state with high-conversion quantum efficiency, while it is forbidden in the thermodynamic process. In addition, the second-order nonlinear optical response for closed-isomer 1b is nearly six times larger than that for open-isomer 1a. It is also confirmed that the photoirradiation evokes the photoisomerization character to show dramatic difference in the second-order NLO response, which can be applied to designing photochromic materials and reversible NLO switches.</description><identifier>ISSN: 1089-5639</identifier><identifier>EISSN: 1520-5215</identifier><identifier>DOI: 10.1021/jp302535m</identifier><identifier>PMID: 22591243</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Carbon ; Charge ; Dichroism ; Electron transitions ; Mathematical analysis ; Nonlinearity ; Quantum efficiency ; Spectra</subject><ispartof>The journal of physical chemistry. 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A, Molecules, spectroscopy, kinetics, environment, & general theory</title><addtitle>J. Phys. Chem. A</addtitle><description>DFT and TDDFT methods have been performed to investigate the photoisomerization effect for dithiazolylarylene on solution. The weak S···N interaction and CH···N hydrogen bond restrain the rotation of the side-chain thiazolyl ring in open-isomer 1a, the higher stability of which prefers to show a high quantum yield of photoisomerization. The calculated UV–Vis spectrum at around 320 nm for open-isomer 1a is bathochromically shifted to 647 nm for closed-isomer 1b, in excellent agreement with the experimental photochromic phenomenon. The electron transition in ECD (electron circular dichroism) spectra for closed-isomer 1b with two chiral carbon atoms is dominated by ICT (intramolecular charge transition) and LE (local excitation) corresponding to one positive (440 nm) and one negative Cotton effect (650 nm), respectively, where the two chiral carbon atoms play a slight role in these transitions. The PES in the S1 and S0 states, respectively, indicates that the cyclization reaction from open-isomer 1a to closed-isomer 1b is allowed in the photoexcited state with high-conversion quantum efficiency, while it is forbidden in the thermodynamic process. In addition, the second-order nonlinear optical response for closed-isomer 1b is nearly six times larger than that for open-isomer 1a. It is also confirmed that the photoirradiation evokes the photoisomerization character to show dramatic difference in the second-order NLO response, which can be applied to designing photochromic materials and reversible NLO switches.</description><subject>Carbon</subject><subject>Charge</subject><subject>Dichroism</subject><subject>Electron transitions</subject><subject>Mathematical analysis</subject><subject>Nonlinearity</subject><subject>Quantum efficiency</subject><subject>Spectra</subject><issn>1089-5639</issn><issn>1520-5215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqF0ctq3DAUBmBRGnJf9AWKNoVk4eToNiMvS-4QktIkayPLx4wG2XIlO2Hy9FGYaVaBrHT4-fhB5xDyg8EJA85Ol4MAroTqvpFdpjgUijP1Pc-gy0LNRLlD9lJaAgATXG6THc5VybgUu2R4XGCIODprPH0Yp2ZFQ0__LMIYXAodRvdqRpeji7ZFO9IXNy6ooX_xGWNytUd6F3rvejSR3g-bmozsgrYh0vPMnXkNfuVNXHns8YBstcYnPNy8--Tp8uLx7Lq4vb-6Oft9Wxgh9VhoaaFRzHJuywYFaq2Fns9R5IgJy8EwyRS0iFDzRtZ1rayelTnRrAZAsU-O1r1DDP8mTGPVuWTRe9NjmFLF5krIUmoJX1Ng5YyVc9CZHq-pjSGliG01RNflr2VUvd-i-rhFtj83tVPdYfMh_y8_g19rYGyqlmGKfV7IJ0Vvn6qRMQ</recordid><startdate>20120607</startdate><enddate>20120607</enddate><creator>Song, Ping</creator><creator>Gao, Ai-Hua</creator><creator>Zhou, Pan-Wang</creator><creator>Chu, Tian-Shu</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20120607</creationdate><title>Theoretical Study on Photoisomerization Effect with a Reversible Nonlinear Optical Switch for Dithiazolylarylene</title><author>Song, Ping ; Gao, Ai-Hua ; Zhou, Pan-Wang ; Chu, Tian-Shu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a348t-84c0d51c22c9de3e8883877e31c213c20a14150fee0b2d4bbb5c86950f81b00e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Carbon</topic><topic>Charge</topic><topic>Dichroism</topic><topic>Electron transitions</topic><topic>Mathematical analysis</topic><topic>Nonlinearity</topic><topic>Quantum efficiency</topic><topic>Spectra</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Song, Ping</creatorcontrib><creatorcontrib>Gao, Ai-Hua</creatorcontrib><creatorcontrib>Zhou, Pan-Wang</creatorcontrib><creatorcontrib>Chu, Tian-Shu</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Song, Ping</au><au>Gao, Ai-Hua</au><au>Zhou, Pan-Wang</au><au>Chu, Tian-Shu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Theoretical Study on Photoisomerization Effect with a Reversible Nonlinear Optical Switch for Dithiazolylarylene</atitle><jtitle>The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory</jtitle><addtitle>J. Phys. Chem. A</addtitle><date>2012-06-07</date><risdate>2012</risdate><volume>116</volume><issue>22</issue><spage>5392</spage><epage>5397</epage><pages>5392-5397</pages><issn>1089-5639</issn><eissn>1520-5215</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>DFT and TDDFT methods have been performed to investigate the photoisomerization effect for dithiazolylarylene on solution. The weak S···N interaction and CH···N hydrogen bond restrain the rotation of the side-chain thiazolyl ring in open-isomer 1a, the higher stability of which prefers to show a high quantum yield of photoisomerization. The calculated UV–Vis spectrum at around 320 nm for open-isomer 1a is bathochromically shifted to 647 nm for closed-isomer 1b, in excellent agreement with the experimental photochromic phenomenon. The electron transition in ECD (electron circular dichroism) spectra for closed-isomer 1b with two chiral carbon atoms is dominated by ICT (intramolecular charge transition) and LE (local excitation) corresponding to one positive (440 nm) and one negative Cotton effect (650 nm), respectively, where the two chiral carbon atoms play a slight role in these transitions. The PES in the S1 and S0 states, respectively, indicates that the cyclization reaction from open-isomer 1a to closed-isomer 1b is allowed in the photoexcited state with high-conversion quantum efficiency, while it is forbidden in the thermodynamic process. In addition, the second-order nonlinear optical response for closed-isomer 1b is nearly six times larger than that for open-isomer 1a. It is also confirmed that the photoirradiation evokes the photoisomerization character to show dramatic difference in the second-order NLO response, which can be applied to designing photochromic materials and reversible NLO switches.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>22591243</pmid><doi>10.1021/jp302535m</doi><tpages>6</tpages></addata></record> |
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subjects | Carbon Charge Dichroism Electron transitions Mathematical analysis Nonlinearity Quantum efficiency Spectra |
title | Theoretical Study on Photoisomerization Effect with a Reversible Nonlinear Optical Switch for Dithiazolylarylene |
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