基于1,8-萘啶双硼核化合物的合成、结构及光谱性质研究

doi:10.7517/j.issn.1674-0475.2013.01.006

影像科学与光化学 ›› 2013, Vol. 31 ›› Issue (1): 42-52.DOI: 10.7517/j.issn.1674-0475.2013.01.006

基于1,8-萘啶双硼核化合物的合成、结构及光谱性质研究

权莉^1,2, 陈勇¹, 吕小军¹, 傅文甫¹

1. 中国科学院理化技术研究所, 北京 100190;
2. 中国科学院研究生院, 北京 100049

收稿日期:2012-05-11 修回日期:2012-06-05 出版日期:2013-01-15 发布日期:2013-01-15
通讯作者: 傅文甫,男,研究员,通讯联系人, E-mail:fuwf@mail.ipc.ac.cn.

Synthesis, Structure and Photophysical Properties of a 1,8-Naphthyridine-BF₂ Complex

QUAN Li^1,2, CHEN Yong¹, LU Xiao-jun¹, FU Wen-fu¹

1. Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China;
2. Graduated University of Chinese Academy of Sciences, Beijing 100049, P. R. China

Received:2012-05-11 Revised:2012-06-05 Online:2013-01-15 Published:2013-01-15

摘要/Abstract

摘要： 设计合成了基于萘啶类衍生物1,2-二(7-氯-1,8-萘啶-2)-肼(H₂L)及其双硼核化合物 C1. H₂L的光谱性质具有明显的溶剂效应,它的发光很弱,而 C1的发光很强,荧光量子产率超过90%. H₂L在甲醇中不稳定,其相应的光谱特征蓝移到萘啶的特征峰,但金属离子Hg²⁺和Zn²⁺的引入能够恢复 H₂L的特征峰.通过溶剂挥发的方法得到了 C1的单晶.结构研究表明,在其晶胞中分子间通过C3-H3…F1和C3-H3…F2氢键作用形成三维网格结构.

关键词: 萘啶, 氟硼化合物, 晶体结构, 荧光, 光谱性质

Abstract: The hydrazine ligand (H₂L) bearing naphthyridine moieties and its bis-BF₂ (C1) compound were designed and synthesized. The crystal structure analysis of C1 revealed that molecules in the cell were linked by C3-H3…F1 and C3-H3…F2 hydrogen bonds to form a 3D network structure. Spectroscopic properties of H₂L are sensitive to solvents. The absorption spectrum of H₂L in MeOH was blue-shifted with respect to that in CH₂Cl₂, and which can be restored upon addition of metal ions. C1 exhibits intense fluorescence in MeOH with a quantum yield of 0.92.

Key words: naphthyridine, BF₂-compound, crystal structure, fluorescence, spectroscopic properties

中图分类号:

权莉, 陈勇, 吕小军, 傅文甫. 基于1,8-萘啶双硼核化合物的合成、结构及光谱性质研究[J]. 影像科学与光化学, 2013, 31(1): 42-52.

QUAN Li, CHEN Yong, LU Xiao-jun, FU Wen-fu. Synthesis, Structure and Photophysical Properties of a 1,8-Naphthyridine-BF₂ Complex[J]. Imaging Science and Photochemistry, 2013, 31(1): 42-52.

参考文献

[1] Matveeva A G, Lemport P S, Pasechnik M P, Aysin R R, Leites L A, Nifantev E E. Coordination of 2-phosphorylalkyl-substituted 1, 8-naphthyridines in complexes with lanthanide nitrates[J]. Russ. Chem. B., In. Ed., 2009, 58(7): 1416-1422.
[2] Chen Y, Zhao X J, Gan X, Fu W F. Zinc(Ⅱ) complexes with 1,8-naphthyridine-based ligand: crystal structures and luminescent properties[J].Inorg. Chim. Acta, 2008, 361: 2335-2342.
[3] Boens N, Leen V, Dehaen W. Fluorescent indicators based on BODIPY[J]. Chem. Soc. Rev., 2012, 41: 1130-1172.
[4] Loudet A, Burgess K. BODIPY dyes and their derivatives: syntheses and spectroscopic properties[J]. Chem. Rev., 2007, 107: 4891-4932.
[5] Ulrich G, Ziessel R, Harriman A. The chemistry of fluorescent bodipy dyes: versatility unsurpassed[J]. Angew. Chem., Int. Ed., 2008, 47(7):1184-1201.
[6] Nagai A, Kokado K, Nagata Y, Arita M, Chujo Y. Highly intense fluorescent diarylboron diketonate[J]. J. Org. Chem., 2008, 73(21): 8605-8607.
[7] Maeda H, Mihashi Y, Haketa Y. Heteroaryl-substituted C3-bridged oligopyrroles: potential building subunits of anion-responsive π-conjugated oligomers[J]. Org. Lett., 2008, 10(15): 3179-3182.
[8] Zhang G, Lu J, Sabat M, Fraser C L. Polymorphism and reversible mechanochromic luminescence for solid-state difluoroboron avobenzone[J]. J. Am. Chem. Soc., 2010, 132(7): 2160-2162.
[9] Poon C T, Lam W H, Wong H L, Yam V W W. A versatile photochromic dithienylethene-containing β-diketonate ligand: near-infrared photochromic behavior and photoswitchable luminescence properties upon incorporation of a boron(III) center[J]. J. Am. Chem. Soc., 2010, 132(40): 13992-13993.
[10] Stefane B. Selective addition of organolithium reagents to BF₂-chelates of β-ketoesters[J]. Org. Lett., 2010, 12(13): 2900-2903.
[11] Kubota Y, Tsuzuki T, Funabiki K, Ebihara M, Matsui M. Synthesis and fluorescence properties of a pyridomethene- BF₂ complex[J]. Org. Lett., 2010, 12(18): 4010-4013.
[12] Hayashi S, Inokuma Y, Osuka A. Meso-tris(oligo-2,5-thienylene)-substituted subporphyrins[J]. Org. Lett., 2010, 12(18): 4148-4151.
[13] Yoshino J, Kano N, Kawashima T. Synthesis of the most intensely fluorescent azobenzene by utilizing the B—N interaction[J]. Chem. Commun., 2007: 559-561.
[14] Job A, Wakamiya A, Kehr G, Erker G, Yamaguchi S. Electronic tuning of thiazolyl-capped π-conjugated compounds via a coordination/cyclization protocol with B(C₆F₅)₃[J]. Org. Lett., 2010, 12(23): 5470-5473.
[15] Fu W F, Li H F J, Wang D H. A novel Kolbe reaction pathway for a selective one- and two-electron reduction of azo compounds[J]. Chem. Commun., 2009, 5524-5526.
[16] Bröring M, Krüger R, Link S. Bis(BF₂)-2, 2'-bidipyrrins (BisBODIPYs): highly fluorescent BODIPY dimers with large stokes shifts[J]. Chem. Eur. J., 2008, 14(10): 2976-2983.
[17] Ono K, Hashizume J, Yamaguchi H, Tomura M, Nishida J, Yamashita Y. Synthesis, crystal structure, and electron-accepting property of the BF₂ complex of a dihydroxydione with a perfluorotetracene skeleton[J]. Org. Lett., 2009, 11(19): 4326-4329.
[18] Launary J P, Tourrel-Pagis M, Lipskier J F. Control of intramolecular electron transfer by a chemical reaction. The 4,4'-azopyridine/1,2-bis(4-pyridyl)hydrazine system[J]. Inorg. Chem., 1991, 30(5):1033-1038.
[19] Chen Y, Fu W F, Li J L, Zhao X J, Ou X M. Conformation impact on spectral properties of bis(5,7-dimethyl-1,8-naphthyridin-2-yl)amine and its Zn-II complex[J]. New J. Chem., 2007, 31(10): 1785-1788.
[20] Chen Y, Chen J S, Gan X, Fu W F. Dinuclear copper(Ⅰ) complexes containing diimine and phosphine ligands: synthesis, copper-copper separation and photophysical properties[J]. Inorg. Chim. Acta, 2009, 362(7): 2492-2498.
[21] Zuo J L, Fu W F, Che C M, Cheung K K. Synthesis, crystal structure, and photoluminescent properties of a tetracarbonyl(naphthyridylearbamoyl) rhenium(I) complex and a highly emissive tetracarbonyl (naphthyridylamido) rhenium(I) complex[J]. Eur. J. Inorg. Chem., 2003, 2: 255-262.
[22] Sadhukhan N, Bera J K. Mixed-metal assemblies involving ferrocene -naphthyridine hybrids[J]. Inorg. Chem., 2009, 48(3): 978-990.
[23] Brown E V, Granneman G R. Cis-trans isomerism in the pyridyl analogs of azobenzene.A kinetic and molecular orbital analysis[J]. J. Am. Chem. Soc., 1975, 97(3): 621-627.
[24] Yang Y, Su X, Carroll C N, Aprahamian I. Aggregation-induced emission in BF₂-hydrazone (BODIHY) complexes[J]. Chem. Sci., 2012, 3: 610-613.
[25] Li H F J, Fu W F, Li L, Gan X, Mu W H, Chen W Q, Duan X M, Song H B. Intense one- and two-photon excited fluorescent bis(BF₂) core complex containing a 1,8-naphthyridine derivative[J]. Org. Lett., 2010, 12(13): 2924-2927.
[26] McDonnell S O, OShea D F. Near-infrared sensing properties of dimethlyamino-substituted BF₂-azadipyrromethenes[J]. Org. Lett., 2006, 8(16): 3493-3496.
[27] Yamaguchi S, Akiyama S. Kohei Tamao. Tri-9-anthrylborane and its derivatives: new boron-containing π-electron systems with divergently extended π-conjugation through boron [J]. J. Am. Chem. Soc., 2000, 122(26): 6335-6336.
[28] Camerel F, Bonardi L, Schmutz M, Ziessel R. Highly luminescent gels and mesogens based on elaborated borondipyrromethenes[J]. J. Am. Chem. Soc., 2006, 128(14): 4548-4549.
[29] Chen Y, Fu W F, Li J L, Zhao X J, Ou X M. Conformation impact on spectral properties of bis(5,7-dimethyl-1,8-naphthyridin-2-yl)amine and its Zn^Ⅱ complex [J]. New J. Chem., 2007, 31: 1785-1788.

基于1,8-萘啶双硼核化合物的合成、结构及光谱性质研究

Synthesis, Structure and Photophysical Properties of a 1,8-Naphthyridine-BF₂ Complex

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	黄海清, 肖赛金, 杨光赵耀, 赵家辉. 氧化钼量子点无标记快速ATP检测[J]. 影像科学与光化学, 2020, 38(6): 950-955.
[2]	马逸骅, 陈琳, 杨永珍, 于世平, 苏秀琴. 钆掺杂碳量子点的制备及其双模态成像研究进展[J]. 影像科学与光化学, 2020, 38(5): 763-770.
[3]	岳帅, 邵竹梅, 姜新东. 近红外荧光BODIPY/aza-BODIPY染料的研究进展[J]. 影像科学与光化学, 2020, 38(4): 585-600.
[4]	贾红丹, 邢文莉, 宋玉姣, 郑社洪, 高云燕, 欧植泽. 负载于二氧化硅纳米粒子的菲并咪唑衍生物对Hg²⁺的检测[J]. 影像科学与光化学, 2020, 38(4): 601-608.
[5]	朱文庆, 樊盼, 李扬, 朱玉梦, 张瑾. 双配体Zn(Ⅱ)MOFs材料的构筑及光致发光性能[J]. 影像科学与光化学, 2020, 38(2): 159-166.
[6]	李箫宁, 李檬. 改性凹凸棒的制备及对砷离子的吸附研究[J]. 影像科学与光化学, 2019, 37(2): 127-135.
[7]	刘晓琴, 黄媛媛, 高建峰, 陈玉哲, 佟振合, 吴骊珠. 双光子激发的超分子聚合物纳米颗粒生物成像研究[J]. 影像科学与光化学, 2019, 37(2): 136-145.
[8]	蒋伟, 房慧颖, 何晓静. 磁共振/光学双模态分子探针的研究现状与展望[J]. 影像科学与光化学, 2019, 37(2): 156-162.
[9]	李亚丽, 郭靖, 宋娟, 朴向民, 徐晓龙, 王英平. 荧光碳点探针的合成、性质及其在生物成像中的应用[J]. 影像科学与光化学, 2019, 37(1): 46-56.
[10]	王凯霞, 徐炜, 贺庆国, 程建功. 高选择性甲基苯丙胺蒸气检测用荧光探针的设计、合成及性能[J]. 影像科学与光化学, 2018, 36(6): 478-488.
[11]	张战胜, 高杨晨, 沈敦璞, 谢垠蓬, 李明, 王猛. 铕荧光配合物的合成及其在手印显现中的应用[J]. 影像科学与光化学, 2018, 36(6): 498-506.
[12]	常顺周, 相开强, 明伟, 张志忠, 田宝柱, 张金龙. 一种基于PET机理pH荧光探针的合成及其性能研究[J]. 影像科学与光化学, 2018, 36(5): 425-433.
[13]	王娟娟, 魏学红. 温度对激光扫描共聚焦成像效果的影响[J]. 影像科学与光化学, 2018, 36(5): 443-452.
[14]	李俊芬, 李鹏霞, 张琳, 董川. 1,5-二苯基-3-联苯基-2-吡唑啉的荧光光谱行为研究[J]. 影像科学与光化学, 2018, 36(4): 299-305.
[15]	谢先格, 夏方媛, 黄苏琴, 彭小伟, 傅燕, 王筱梅, 陶绪堂. 罗丹明6G螺环酰肼荧光快速检测谷氨酸和天门冬氨酸[J]. 影像科学与光化学, 2018, 36(4): 315-323.

基于1,8-萘啶双硼核化合物的合成、结构及光谱性质研究

Synthesis, Structure and Photophysical Properties of a 1,8-Naphthyridine-BF2 Complex

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

Synthesis, Structure and Photophysical Properties of a 1,8-Naphthyridine-BF₂ Complex