Second-order nonlinear optical properties of dithienophenazine and TTF derivatives: A butterfly effect of dimalononitrile substitutions
•First hyperpolarizabilities were calculated for phenazine and TTF merged derivatives.•Substitutions of dimalononitrile groups at phenazine part robust the first hyperpolarizability.•TD-DFT study has been performed to trace the origin of larger β amplitudes. Using density functional theory (DFT) met...
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| description | •First hyperpolarizabilities were calculated for phenazine and TTF merged derivatives.•Substitutions of dimalononitrile groups at phenazine part robust the first hyperpolarizability.•TD-DFT study has been performed to trace the origin of larger β amplitudes.
Using density functional theory (DFT) methods, the nonlinear optical (NLO) properties have been calculated with strong donor-π-conjugation-acceptor configurations. The static first hyperpolarizability (β0) and dynamic (frequency dependent) electric field induced second harmonic generation (EFISHG) first hyperpolarizability (μβ) are calculated for all designed systems. Our DFT calculations show dithienophenazine merged TTF (2) holds larger β0 amplitudes (β0=21.04×103a.u.) as compared to its corresponding compounds of TTF merged-difurophenazine (1), dicyclopentaphenazine (3) and dipyrrolophenazine (4) derivatives having β0 amplitudes of 16.25×103, 12.69×103, and 18.38×103a.u., respectively. Furthermore, substitution of dimalononitrile [C(CN)2]2 groups at acceptor end of these compounds results in new derivatives 1a–4a, respectively. Interestingly, a butterfly effect on first hyperpolarizability of all systems 1a–4a has been spotted, which not only results in their robustly larger β0 amplitudes but also changes the increasing order of β0 amplitudes from systems 3 |
| doi_str_mv | 10.1016/j.jmgm.2015.03.003 |
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Using density functional theory (DFT) methods, the nonlinear optical (NLO) properties have been calculated with strong donor-π-conjugation-acceptor configurations. The static first hyperpolarizability (β0) and dynamic (frequency dependent) electric field induced second harmonic generation (EFISHG) first hyperpolarizability (μβ) are calculated for all designed systems. Our DFT calculations show dithienophenazine merged TTF (2) holds larger β0 amplitudes (β0=21.04×103a.u.) as compared to its corresponding compounds of TTF merged-difurophenazine (1), dicyclopentaphenazine (3) and dipyrrolophenazine (4) derivatives having β0 amplitudes of 16.25×103, 12.69×103, and 18.38×103a.u., respectively. Furthermore, substitution of dimalononitrile [C(CN)2]2 groups at acceptor end of these compounds results in new derivatives 1a–4a, respectively. Interestingly, a butterfly effect on first hyperpolarizability of all systems 1a–4a has been spotted, which not only results in their robustly larger β0 amplitudes but also changes the increasing order of β0 amplitudes from systems 3<1<4<2 to 1a<2a<3a<4a at both PBE0/6-31G* and CAM-B3LYP/6-31+G* levels of theory. For example, the increase in β0 amplitudes of systems 1a, 2a, 3a and 4a are 3, 3, 5, and 19 times as compared with their corresponding non dimalononitrile derivatives at PBE0/6-31G* level of theory, respectively. Remarkably, unlike the static first hyperpolarizability, the dynamic EFISHG hyperpolarizability (μβω) has the largest value for system 4a with its amplitudes of 1378.59×10−46 and 1349.40×10−46esu, at PBE0/6-31G* and CAM-B3LYP/6-31+G* levels of theory, respectively. TD-DFT calculations have been performed to trace the origin of first hyperpolarizability. It has been found that the lower transition energy and higher oscillator strengths cause robustly large amplitudes especially in systems 3a and 4a, which consequently stems in strong donor-π-conjugation-acceptor configuration of these systems. Thus the present results intrigue the butterfly effect of a two-step substitution on NLO properties of TTF merged dithienophenazine compounds that can be used as an efficient NLO material.]]></description><identifier>ISSN: 1093-3263</identifier><identifier>EISSN: 1873-4243</identifier><identifier>DOI: 10.1016/j.jmgm.2015.03.003</identifier><identifier>PMID: 25863481</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Amplitudes ; Butterflies ; Derivatives ; Dithienophenazine merged TTF derivatives ; Donor-π-conjugation-acceptor model ; Dynamical systems ; Dynamics ; Electric field induced second harmonic generation (EFISHG) ; Electrons ; First hyperpolarizability ; Mathematical models ; Models, Molecular ; Molecular Conformation ; Nitriles - chemistry ; Nonlinear optical property ; Nonlinearity ; Optical properties ; Phenazines - chemistry ; Quantum Theory</subject><ispartof>Journal of molecular graphics & modelling, 2015-06, Vol.59, p.14-20</ispartof><rights>2015 Elsevier Inc.</rights><rights>Copyright © 2015 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c488t-7ad45361f37fa5df331e6b5164d07029079c638ed49e1dfde6b8164d280b95ca3</citedby><cites>FETCH-LOGICAL-c488t-7ad45361f37fa5df331e6b5164d07029079c638ed49e1dfde6b8164d280b95ca3</cites><orcidid>0000-0003-4908-3313</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S1093326315000534$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25863481$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Muhammad, Shabbir</creatorcontrib><title>Second-order nonlinear optical properties of dithienophenazine and TTF derivatives: A butterfly effect of dimalononitrile substitutions</title><title>Journal of molecular graphics & modelling</title><addtitle>J Mol Graph Model</addtitle><description><![CDATA[•First hyperpolarizabilities were calculated for phenazine and TTF merged derivatives.•Substitutions of dimalononitrile groups at phenazine part robust the first hyperpolarizability.•TD-DFT study has been performed to trace the origin of larger β amplitudes.
Using density functional theory (DFT) methods, the nonlinear optical (NLO) properties have been calculated with strong donor-π-conjugation-acceptor configurations. The static first hyperpolarizability (β0) and dynamic (frequency dependent) electric field induced second harmonic generation (EFISHG) first hyperpolarizability (μβ) are calculated for all designed systems. Our DFT calculations show dithienophenazine merged TTF (2) holds larger β0 amplitudes (β0=21.04×103a.u.) as compared to its corresponding compounds of TTF merged-difurophenazine (1), dicyclopentaphenazine (3) and dipyrrolophenazine (4) derivatives having β0 amplitudes of 16.25×103, 12.69×103, and 18.38×103a.u., respectively. Furthermore, substitution of dimalononitrile [C(CN)2]2 groups at acceptor end of these compounds results in new derivatives 1a–4a, respectively. Interestingly, a butterfly effect on first hyperpolarizability of all systems 1a–4a has been spotted, which not only results in their robustly larger β0 amplitudes but also changes the increasing order of β0 amplitudes from systems 3<1<4<2 to 1a<2a<3a<4a at both PBE0/6-31G* and CAM-B3LYP/6-31+G* levels of theory. For example, the increase in β0 amplitudes of systems 1a, 2a, 3a and 4a are 3, 3, 5, and 19 times as compared with their corresponding non dimalononitrile derivatives at PBE0/6-31G* level of theory, respectively. Remarkably, unlike the static first hyperpolarizability, the dynamic EFISHG hyperpolarizability (μβω) has the largest value for system 4a with its amplitudes of 1378.59×10−46 and 1349.40×10−46esu, at PBE0/6-31G* and CAM-B3LYP/6-31+G* levels of theory, respectively. TD-DFT calculations have been performed to trace the origin of first hyperpolarizability. It has been found that the lower transition energy and higher oscillator strengths cause robustly large amplitudes especially in systems 3a and 4a, which consequently stems in strong donor-π-conjugation-acceptor configuration of these systems. Thus the present results intrigue the butterfly effect of a two-step substitution on NLO properties of TTF merged dithienophenazine compounds that can be used as an efficient NLO material.]]></description><subject>Amplitudes</subject><subject>Butterflies</subject><subject>Derivatives</subject><subject>Dithienophenazine merged TTF derivatives</subject><subject>Donor-π-conjugation-acceptor model</subject><subject>Dynamical systems</subject><subject>Dynamics</subject><subject>Electric field induced second harmonic generation (EFISHG)</subject><subject>Electrons</subject><subject>First hyperpolarizability</subject><subject>Mathematical models</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Nitriles - chemistry</subject><subject>Nonlinear optical property</subject><subject>Nonlinearity</subject><subject>Optical properties</subject><subject>Phenazines - chemistry</subject><subject>Quantum Theory</subject><issn>1093-3263</issn><issn>1873-4243</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkU2P1SAUhonROB_6B1wYlm5aoRRKjZvJxHFMJnHhdU0oHBxuWqhAbzL-Af-23NzRpbqC5DzvIbwPQq8oaSmh4u2-3S_flrYjlLeEtYSwJ-icyoE1fdezp_VORtawTrAzdJHznlRCkuE5Ouu4FKyX9Bz9_AImBtvEZCHhEMPsA-iE41q80TNeU1whFQ8ZR4etL_ceQlzvIegflcQ6WLzb3eCa9gdd_AHyO3yFp60USG5-wOAcmHIKL3qO9Qlfkp8B523KxZet-BjyC_TM6TnDy8fzEn29-bC7vm3uPn_8dH1115heytIM2vacCerY4DS3jjEKYuJU9JYMpBvJMBrBJNh-BGqdrUN5HHaSTCM3ml2iN6e99WPfN8hFLT4bmGcdIG5Z0WEgbJBS0v9AGR87Usl_o0KKnvKRjxXtTqhJMecETq2pFpMeFCXqqFXt1VGrOmpVhKkqrYZeP-7fpgXsn8hvjxV4fwKgdnfwkFQ2VZQB61OtX9no_7b_F9JPtfc</recordid><startdate>201506</startdate><enddate>201506</enddate><creator>Muhammad, Shabbir</creator><general>Elsevier Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7SC</scope><scope>7U5</scope><scope>JQ2</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><orcidid>https://orcid.org/0000-0003-4908-3313</orcidid></search><sort><creationdate>201506</creationdate><title>Second-order nonlinear optical properties of dithienophenazine and TTF derivatives: A butterfly effect of dimalononitrile substitutions</title><author>Muhammad, Shabbir</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c488t-7ad45361f37fa5df331e6b5164d07029079c638ed49e1dfde6b8164d280b95ca3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amplitudes</topic><topic>Butterflies</topic><topic>Derivatives</topic><topic>Dithienophenazine merged TTF derivatives</topic><topic>Donor-π-conjugation-acceptor model</topic><topic>Dynamical systems</topic><topic>Dynamics</topic><topic>Electric field induced second harmonic generation (EFISHG)</topic><topic>Electrons</topic><topic>First hyperpolarizability</topic><topic>Mathematical models</topic><topic>Models, Molecular</topic><topic>Molecular Conformation</topic><topic>Nitriles - chemistry</topic><topic>Nonlinear optical property</topic><topic>Nonlinearity</topic><topic>Optical properties</topic><topic>Phenazines - chemistry</topic><topic>Quantum Theory</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Muhammad, Shabbir</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>ProQuest Computer Science Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><jtitle>Journal of molecular graphics & modelling</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Muhammad, Shabbir</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Second-order nonlinear optical properties of dithienophenazine and TTF derivatives: A butterfly effect of dimalononitrile substitutions</atitle><jtitle>Journal of molecular graphics & modelling</jtitle><addtitle>J Mol Graph Model</addtitle><date>2015-06</date><risdate>2015</risdate><volume>59</volume><spage>14</spage><epage>20</epage><pages>14-20</pages><issn>1093-3263</issn><eissn>1873-4243</eissn><abstract><![CDATA[•First hyperpolarizabilities were calculated for phenazine and TTF merged derivatives.•Substitutions of dimalononitrile groups at phenazine part robust the first hyperpolarizability.•TD-DFT study has been performed to trace the origin of larger β amplitudes.
Using density functional theory (DFT) methods, the nonlinear optical (NLO) properties have been calculated with strong donor-π-conjugation-acceptor configurations. The static first hyperpolarizability (β0) and dynamic (frequency dependent) electric field induced second harmonic generation (EFISHG) first hyperpolarizability (μβ) are calculated for all designed systems. Our DFT calculations show dithienophenazine merged TTF (2) holds larger β0 amplitudes (β0=21.04×103a.u.) as compared to its corresponding compounds of TTF merged-difurophenazine (1), dicyclopentaphenazine (3) and dipyrrolophenazine (4) derivatives having β0 amplitudes of 16.25×103, 12.69×103, and 18.38×103a.u., respectively. Furthermore, substitution of dimalononitrile [C(CN)2]2 groups at acceptor end of these compounds results in new derivatives 1a–4a, respectively. Interestingly, a butterfly effect on first hyperpolarizability of all systems 1a–4a has been spotted, which not only results in their robustly larger β0 amplitudes but also changes the increasing order of β0 amplitudes from systems 3<1<4<2 to 1a<2a<3a<4a at both PBE0/6-31G* and CAM-B3LYP/6-31+G* levels of theory. For example, the increase in β0 amplitudes of systems 1a, 2a, 3a and 4a are 3, 3, 5, and 19 times as compared with their corresponding non dimalononitrile derivatives at PBE0/6-31G* level of theory, respectively. Remarkably, unlike the static first hyperpolarizability, the dynamic EFISHG hyperpolarizability (μβω) has the largest value for system 4a with its amplitudes of 1378.59×10−46 and 1349.40×10−46esu, at PBE0/6-31G* and CAM-B3LYP/6-31+G* levels of theory, respectively. TD-DFT calculations have been performed to trace the origin of first hyperpolarizability. It has been found that the lower transition energy and higher oscillator strengths cause robustly large amplitudes especially in systems 3a and 4a, which consequently stems in strong donor-π-conjugation-acceptor configuration of these systems. Thus the present results intrigue the butterfly effect of a two-step substitution on NLO properties of TTF merged dithienophenazine compounds that can be used as an efficient NLO material.]]></abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>25863481</pmid><doi>10.1016/j.jmgm.2015.03.003</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0003-4908-3313</orcidid></addata></record> |
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| subjects | Amplitudes Butterflies Derivatives Dithienophenazine merged TTF derivatives Donor-π-conjugation-acceptor model Dynamical systems Dynamics Electric field induced second harmonic generation (EFISHG) Electrons First hyperpolarizability Mathematical models Models, Molecular Molecular Conformation Nitriles - chemistry Nonlinear optical property Nonlinearity Optical properties Phenazines - chemistry Quantum Theory |
| title | Second-order nonlinear optical properties of dithienophenazine and TTF derivatives: A butterfly effect of dimalononitrile substitutions |
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