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Article: Second-order polarizability of Y-type triphenylamine chromophores

TitleSecond-order polarizability of Y-type triphenylamine chromophores
Y型三苯胺生色分子的二阶极化率
Authors
KeywordsFluorescence Property (荧光性质)
Second-Order Polarizability (二阶极化率)
Solvatochromic Effect (溶剂效应)
Structure-Property Relationship (构效关系)
Y-Type Chromophore (Y型生色分子)
Issue Date2011
PublisherJilin Daxue (东南大学). The Journal's web site is located at http://www.cjcu.jlu.edu.cn/
Citation
Chemical Journal Of Chinese Universities, 2011, v. 32 n. 12, p. 2787-2794 How to Cite?
高等学校化学学报, 2011, v. 32 n. 12, p. 2787-2794 How to Cite?
AbstractThree Y-type triphenylamine chromophores, N,N-Bis-{4-[1-(2-benzothiazolyl)-1,3-butadiene-4-yl]phenyl} aniline (BBtBPA), N,N-bis-{4-[2-(2-benzothiazolyl)vinyl]phenyl} aniline (BBtVPA), and N,N-bis-{4-[1-(3-cyano-2-dicyanomethylidene-5,5- dimethyl-2,5-dihydro-4-furyl)-1,3-butadiene-4-yl]phenyl} aniline (BCfBPA) and four dipolar ones, 1-(2-benzothiazolyl)-4-[4-(N,N-diphenyl)amino]phenyl-1,3-butadiene (BtAPB), 4-[2-(2-benzothiazolyl)vinyl]-N,N-diphenylaniline (BtVPA), 1-[(3-cyano-2-dicyano methylidene-5,5-dimethyl-2, 5-dihydro)-4-furyl]-4-[4-(N,N-diphenyl)-amino]-phenyl-1,3-butadiene (CfAPB) and 4-[2-(3-cyano-2-dicyanomethylidene-5,5- dimethyl-2,5-dihydro-4-furyl)vinyl]-N,N-diphenylaniline (CfVPA) were synthesized through Knoevenagel reaction, with variations in the electron acceptor substitutes and π-conjugated bridges. Absorption and fluorescence properties of these chromophores were investigated. Maxima absorption in dichloromethane were at 425 nm for BBtVPA, 443 nm for BBtBPA, and 613 nm for BCfBPA, respectively. The fluorescence maxima of BBtVPA and BBtBPA were at 516 and 558 nm, respectively. Compared with their dipolar analogues, the Y-type chromophores present about 30 nm bathochromic-shift of absorption maxima, along with slightly bathochromic-shift of fluorescence maxima. Static second-order polarizabilities β 0 were obtained as 40×10 -30 esu for BBtVPA, 64×10 -30 esu for BBtBPA, and 238×10 -30 esu for BCfBPA, respectively, by solvatochromic method based on the two-level model, while 0.9-2.8 times enhancement of β 0 were observed compared with the dipolar chromophores. Besides, extension of π-conjugation and improvement of electron acceptor strength both increase the β value. Quantum chemical calculations were carried out to aid in better understanding of the structure-property relationship.
通过Knoevenagel反应合成了3个Y型三苯胺生色分子N,N-二{4-[2-(2-苯并噻唑基)乙烯基]苯基}苯胺(BBtVPA)、N,N-二{4-[1-(2-苯并噻唑基)-1,3-丁二烯-4-基]苯基}苯胺(BBtBPA)和N,N-二{4-[1-(2-二氰基甲叉-3-氰基-5,5-二甲基-2,5-二氢-4-呋喃基)-1,3-丁二烯-4-基]苯基}苯胺(BCfBPA), 以及4个一维偶极分子4-[2-(2-苯丙噻唑基)乙烯基]-N,N-二苯基苯胺(BtVPA)、1-(2-苯并噻唑基)-4-[4-(N,N-二苯基)氨基]苯基-1,3-丁二烯(BtAPB)、1-[(2-二氰基甲叉-3-氰基-5,5-二甲基-2,5-二氢)-4-呋喃基]-4-[4-(N,N-二苯基氨基)]苯基-1,3-丁二烯(CfAPB)和4-[2-(2-二氰基甲叉-3-氰基-5,5-二甲基-2,5-二氢呋喃-4-基)乙烯基]-N,N-二苯基苯胺(CfVPA). 测定了生色分子的紫外吸收和荧光性质, 在二氯甲烷中, Y型分子BBtVPA, BBtBPA和BCfBPA的最大吸收波长分别为425, 443和613 nm, 比偶极分子红移了约30 nm, Y型分子BBtVPA和BBtBPA的最大荧光发射峰分别位于516和558 nm, 比偶极分子稍有红移. 根据双能级模型理论, 用溶致变色法测定了生色分子的二阶非线性极化率(β), Y型分子BBtVPA, BBtBPA和BCfBPA的β0分别为40×10-30, 64×10-30和238×10-30 esu, 比相应的偶极分子分别提高了0.9~2.8倍. 结果表明, 提高吸电子基团强度, 增大共轭体系有助于获得更大的β值.
Persistent Identifierhttp://hdl.handle.net/10722/168602
ISSN
2015 Impact Factor: 0.791
2015 SCImago Journal Rankings: 0.211
References

 

DC FieldValueLanguage
dc.contributor.authorLu, Wen_US
dc.contributor.authorQian, Yen_US
dc.date.accessioned2012-10-08T03:21:25Z-
dc.date.available2012-10-08T03:21:25Z-
dc.date.issued2011en_US
dc.identifier.citationChemical Journal Of Chinese Universities, 2011, v. 32 n. 12, p. 2787-2794en_US
dc.identifier.citation高等学校化学学报, 2011, v. 32 n. 12, p. 2787-2794-
dc.identifier.issn0251-0790en_US
dc.identifier.urihttp://hdl.handle.net/10722/168602-
dc.description.abstractThree Y-type triphenylamine chromophores, N,N-Bis-{4-[1-(2-benzothiazolyl)-1,3-butadiene-4-yl]phenyl} aniline (BBtBPA), N,N-bis-{4-[2-(2-benzothiazolyl)vinyl]phenyl} aniline (BBtVPA), and N,N-bis-{4-[1-(3-cyano-2-dicyanomethylidene-5,5- dimethyl-2,5-dihydro-4-furyl)-1,3-butadiene-4-yl]phenyl} aniline (BCfBPA) and four dipolar ones, 1-(2-benzothiazolyl)-4-[4-(N,N-diphenyl)amino]phenyl-1,3-butadiene (BtAPB), 4-[2-(2-benzothiazolyl)vinyl]-N,N-diphenylaniline (BtVPA), 1-[(3-cyano-2-dicyano methylidene-5,5-dimethyl-2, 5-dihydro)-4-furyl]-4-[4-(N,N-diphenyl)-amino]-phenyl-1,3-butadiene (CfAPB) and 4-[2-(3-cyano-2-dicyanomethylidene-5,5- dimethyl-2,5-dihydro-4-furyl)vinyl]-N,N-diphenylaniline (CfVPA) were synthesized through Knoevenagel reaction, with variations in the electron acceptor substitutes and π-conjugated bridges. Absorption and fluorescence properties of these chromophores were investigated. Maxima absorption in dichloromethane were at 425 nm for BBtVPA, 443 nm for BBtBPA, and 613 nm for BCfBPA, respectively. The fluorescence maxima of BBtVPA and BBtBPA were at 516 and 558 nm, respectively. Compared with their dipolar analogues, the Y-type chromophores present about 30 nm bathochromic-shift of absorption maxima, along with slightly bathochromic-shift of fluorescence maxima. Static second-order polarizabilities β 0 were obtained as 40×10 -30 esu for BBtVPA, 64×10 -30 esu for BBtBPA, and 238×10 -30 esu for BCfBPA, respectively, by solvatochromic method based on the two-level model, while 0.9-2.8 times enhancement of β 0 were observed compared with the dipolar chromophores. Besides, extension of π-conjugation and improvement of electron acceptor strength both increase the β value. Quantum chemical calculations were carried out to aid in better understanding of the structure-property relationship.en_US
dc.description.abstract通过Knoevenagel反应合成了3个Y型三苯胺生色分子N,N-二{4-[2-(2-苯并噻唑基)乙烯基]苯基}苯胺(BBtVPA)、N,N-二{4-[1-(2-苯并噻唑基)-1,3-丁二烯-4-基]苯基}苯胺(BBtBPA)和N,N-二{4-[1-(2-二氰基甲叉-3-氰基-5,5-二甲基-2,5-二氢-4-呋喃基)-1,3-丁二烯-4-基]苯基}苯胺(BCfBPA), 以及4个一维偶极分子4-[2-(2-苯丙噻唑基)乙烯基]-N,N-二苯基苯胺(BtVPA)、1-(2-苯并噻唑基)-4-[4-(N,N-二苯基)氨基]苯基-1,3-丁二烯(BtAPB)、1-[(2-二氰基甲叉-3-氰基-5,5-二甲基-2,5-二氢)-4-呋喃基]-4-[4-(N,N-二苯基氨基)]苯基-1,3-丁二烯(CfAPB)和4-[2-(2-二氰基甲叉-3-氰基-5,5-二甲基-2,5-二氢呋喃-4-基)乙烯基]-N,N-二苯基苯胺(CfVPA). 测定了生色分子的紫外吸收和荧光性质, 在二氯甲烷中, Y型分子BBtVPA, BBtBPA和BCfBPA的最大吸收波长分别为425, 443和613 nm, 比偶极分子红移了约30 nm, Y型分子BBtVPA和BBtBPA的最大荧光发射峰分别位于516和558 nm, 比偶极分子稍有红移. 根据双能级模型理论, 用溶致变色法测定了生色分子的二阶非线性极化率(β), Y型分子BBtVPA, BBtBPA和BCfBPA的β0分别为40×10-30, 64×10-30和238×10-30 esu, 比相应的偶极分子分别提高了0.9~2.8倍. 结果表明, 提高吸电子基团强度, 增大共轭体系有助于获得更大的β值.-
dc.languagechien_US
dc.publisherJilin Daxue (东南大学). The Journal's web site is located at http://www.cjcu.jlu.edu.cn/en_US
dc.relation.ispartofChemical Journal of Chinese Universitiesen_US
dc.relation.ispartof高等学校化学学报-
dc.subjectFluorescence Property (荧光性质)en_US
dc.subjectSecond-Order Polarizability (二阶极化率)en_US
dc.subjectSolvatochromic Effect (溶剂效应)en_US
dc.subjectStructure-Property Relationship (构效关系)en_US
dc.subjectY-Type Chromophore (Y型生色分子)en_US
dc.titleSecond-order polarizability of Y-type triphenylamine chromophoresen_US
dc.titleY型三苯胺生色分子的二阶极化率-
dc.typeArticleen_US
dc.identifier.emailLu, W:luwei@hku.hken_US
dc.identifier.authorityLu, W=rp00754en_US
dc.description.naturelink_to_OA_fulltexten_US
dc.identifier.scopuseid_2-s2.0-84855540718en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-84855540718&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume32en_US
dc.identifier.issue12en_US
dc.identifier.spage2787en_US
dc.identifier.epage2794en_US
dc.publisher.placeChinaen_US
dc.identifier.scopusauthoridLu, W=27868087600en_US
dc.identifier.scopusauthoridQian, Y=7402872362en_US
dc.customcontrol.immutablecsl 130820-

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