多芳基吡咯衍生物的发光性质及其应用

doi:10.7517/j.issn.1674-0475.2015.06.441

摘要/Abstract

摘要：

荧光分子在良溶剂中基本不发光或发光较弱,而在聚集状态下发光较强的现象,称为聚集诱导发光(Aggregation-induced emission,AIE)现象,这与传统的聚集导致猝灭(Aggregation-caused quenching,ACQ)现象相反。本文研究了多苯基吡咯衍生物的结构与发光性能的关系。通过比较吡咯衍生物的单晶结构和发光性质发现扭曲的结构可以限制共轭发光基团的分子内旋转(RIR),这是产生AIE现象的主要原因。羧酸化的吡咯衍生物可以对Al³⁺实时、选择性检测。由DMF诱导的三苯基吡咯羧酸衍生物(TPPA)重结晶在固态时出现可控的荧光发射,它具备很好的温度选择性,响应迅速,并可以循环利用,这证明TPPA可以作为一种热响应材料用于温度监控设备中。

关键词: 聚集诱导发光, 多苯基吡咯衍生物, 化学传感器

Abstract:

The luminogenic molecules are nonemissive when dissolved in good solvents but become highly luminescent when aggregated in the solid state, thus behaving exactly opposite to the conventional ACQ luminophores. Aggregation-induced emission (AIE) was coined for this unusual phenomenon. The relationship between the structures and light emission properties of multiaryl-substituted pyrrole derivatives was firstly studied in this review. On comparison of the optical properties and single-crystal structures of these pyrrole derivatives, it is suggested that the more twisted configuration which prevented parallel orientation of conjugated chromophores combined with the restricted intramolecular rotation (RIR) effect was the main cause of the AIE phenomenon. The carboxylated-functionalized derivatives can be used to sensitively, selectively and real-time detect Al³⁺ion. The detection mechanism exhibited an aggregation-induced emission (AIE) characteristic. Triphenylpyrrole containing carboxylic acid (TPPA) was found to have a controllable fluorescence in the solid state when it is crystallized from dimethyl formamide (DMF). The rapid response, high selectivity, good reversibility and solvent-free procedure make TPPA a thermo-responsive material for use in temperature monitoring devices. Induced by DMF,Triphenylpyrrole acid (TPPA) derivatives can recrystallizate with good selectivity of temperature,quick response,and can be recycled.

Key words: aggregation-induced emission, multiaryl-substituted pyrrole, chemosensors

刘派, 陈笛笛, 冯霄, 石建兵, 佟斌, 董宇平. 多芳基吡咯衍生物的发光性质及其应用[J]. 影像科学与光化学, 2015, 33(6): 441-460.

LIU Pai, CHEN Didi, FENG Xiao, SHI Jianbing, TONG Bin, DONG Yuping. Emission Properties and Application of Multiaryl-substituted Pyrroles[J]. Imaging Science and Photochemistry, 2015, 33(6): 441-460.

参考文献

[1] Thomas III S W, Joly G D, Swger T M. Chemical sensors based on amplifying fluorescent conjugated polymers[J]. Chemical Reviews,2007, 107: 1339-1386.
[2] Hoeben F J M, Jonkheijm P, Meijer E W, Schenning A P H J. About supramolecular assemblies of π-conjugated systems[J].Chemical Reviews, 2005, 105: 1491-1546.
[3] Bunz Uwe H F. Poly(aryleneethynylene)s: syntheses, properties, structures, and applications[J]. Chemical Reviews, 2000, 100: 1605-1644.
[4] Hide F, Díaz-García M A, Schwartz B J, Heeger A J. New developments in the photonic applications of conjugated polymers[J]. Accounts of Chemical Research, 1997, 30: 430-436.
[5] Borisov S M, Wolfbeis O S. Optical Biosensors[J]. Chem-ical Reviews, 2008, 108: 426-461.
[6] Birks J B. Photophysics of Aromatic Molecules[M].London:John Wiley & Sons Ltd, 1970.
[7] Wang J, Zhao Y F, Dou C D, Sun H, Xu P, Ye K Q, Zhang J Y, Jiang S J, Li F, Wang Y. Alkyl and dendronsubstituted quinacridones: synthesis, structures, and luminescent properties[J]. The Journal of Physical Chemistry B, 2007, 111: 5082-5089.
[8] Hecht S, Fréchet M J. Dendritic Encapsulation of Function: Applying nature's site isolation principle from biomimetics to materials science[J]. Angewandte Chemie International Edition, 2001, 40: 74-91.
[9] Chen L H, Xu S, McBranch D, Whitten D. Tuning the properties of conjugated polyelectrolytes through surfactant complexation[J]. Journal of the American Chemical Society, 2000, 122: 9302-9303.
[10] Luo J D, Xie Z L, Lam J W Y, Cheng L, Chen H Y, Qiu C F, Kwok H S, ZhanX W, Liu Y Q, Zhu D B, Tang B Z.Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole [J]. Chemical Communications, 2001,18: 1740-1741.
[11] Mei J, Hong Y N, Lam J W Y, Qin A J, Tang Y H, Tang B Z. Aggregation-induced emission: The whole is more brilliant than the parts [J]. Advanced Materials, 2014, 26: 5429-5479.
[12] Hong Y N,Lam J W Y,Tang B Z.Aggregation-induced emission[J]. Chemical Society Reviews, 2011,40: 5361-5388.
[13] Li Z, Dong Y Q, Mi B X, Tang Y H, Haussler M, Tong H, Dong Y P, Lam J W Y, Ren Y, Sung H H Y, Wong K S, Gao P, Williams I D, Kwok H S, Tang B Z. Structural control of the photoluminescence of silole regioisomers and their utility as sensitive regiodiscriminating chemosensors and efficient electroluminescent materials [J]. The Journal of Physical Chemistry B,2005, 109: 10061-10066.
[14] Zhao Z J, Lam J W Y, Tang B Z. Aggregation-induced emission of luminogens [J]. Current Organic Chemistry,2010, 14: 2109-2132.
[15] Li K, Ding D, Zhao Q L, Sun J Z, Tang B Z, Liu B. Biocompatible organic dots with aggregation-induced emission for in vitro and in vivo fluorescence imaging [J]. Science China Chemistry,2013, 56: 1228-1233.
[16] 夏晶,吴燕梅,张亚玲,佟斌,石建兵,支俊格,董宇平.具有聚集诱导发光特性的四苯基乙烯研究进展[J].影像科学与光化学,2012, 30(1): 9-25. Xia J, Wu Y M, Zhang Y L, Tong B, Shi J b, Zhi J G, Dong Y P. Recent progress of tetraphenylethenes with aggregation induced emission[J]. Imaging Science and Photochemistry,2012, 30(1): 9-25.
[17] 曾毅,李鹏,李嫕.四苯基乙烯衍生物光物理和光化学研究[J].影像科学与光化学,2014,32(5): 463-470. Zeng Y, Li P, Li Y. Photophysical and photochemical studies on a tetraphenylethene derivative [J]. Imaging Science and Photochemistry, 2014, 32(5): 463-470.
[18] 金佳科,陈秀娟,刘一,秦安军,孙景志, 唐本忠.用水溶性四苯基乙烯基荧光探针检测ctDNA[J].高分子学报, 2011,9: 1079-1085. Jin J K, Chen X J, Liu Y, Qin A J, Sun J Z, Tang B Z.Detection of ctDNA with water soluble tetraphenylene-based fluorescence probe[J]. Acta Polymerica Sinica,2011, 9: 1079-1085.
[19] He J T, Xu B, Chen F P, Xia H J, Li K P, Ye L, Tian W J. Aggregation-induced emission in the crystals of 9,10-distyrylanthracene derivatives: the essential role of restricted intramolecular torsion [J]. Journal of Physical Chemistry C,2009, 113: 9892-9899.
[20] Song N, Chen D X, Xia M C, Qiu X L, Ma K, Xu B, Tian W J, Yang Y W. Supramolecular assembly-induced yellow emission of 9,10-distyrylanthracene bridged bis(pillararene)s[J]. Chemical Communications,2015, 51: 5526-5529.
[21] Dong Y Q, Lam J W Y, Qin A J. Switching the light emission of (4-biphenylyl) fulvene by morphological modulation:crystallization-induced emission enhancement [J]. Chemical Communications,2007,1: 40-42.
[22] Dong S C, Li Z, Qin Z G. New Carbazole-based fluorophores: synthesis, characterization, and aggregation-induced emission enhancement[J].The Journal of Physical Chemistry B, 2009, 113: 434-441.
[23] 杨志涌, 于涛, 陈美娜, 张锡奇, 王程程, 许炳佳, 周勰, 刘四委, 张艺,池振国, 许家瑞. 具有聚集诱导发光效应的咔唑基三苯乙烯衍生物单体及聚合物 [J].高分子学报, 2009, 6: 560-565. Yang Z Y, Yu T, Chen M N, Zhang X Q, Wang C C, Xu B J, Zhou X, Liu S W, Zhang Y, Chi Z G, Xu J R.A monomer and its polymer derived from carbazolyl triphenylene with aggregation induced emission effect characteristics[J]. Acta Polymerica Sinica,2009, 6: 560-565.
[24] An B K, Gierschner J, Park S Y. Pi-conjugated cyanostilbene derivatives: aunique self-assembly motif for molecular manostructures with enhanced emission and transport [J]. Accounts of Chemical Research,2012, 45: 544-554.
[25] Han T, Zhang Y J, Feng X, Lin Z, Tong B, Shi J B, Zhi J G, Dong Y P. Reversible and hydrogen bonding-assisted piezochromic luminescence for solid-state tetraaryl-buta-1,3-diene [J]. Chemical Communications,2013, 49: 7049-7051.
[26] Zhang Y J, Han T, Gu, S Z, Zhou T Y, Zhao C Z, Guo Y X, Feng X, Tong B, Bing J.; Shi J B, Zhi J G, Dong Y P. Mechanochromic behavior of aryl-substituted buta-1,3-diene derivatives with aggregation enhanced emission[J].Chemistry -A European Journal,2014, 20: 8856- 8861.
[27] Zhang Y H,Kong L W,Shi J B, Tong B, Zhi J G, Feng X, Dong Y P. Aggregation-induced emission of hexaphenyl-1,3-butadiene [J]. Chinese Journal of Chemistry, 2015, 33: 701-704.
[28] Zeng Q, Li Z, Dong Y, Di C, Qin A,Hong Y, Ji L, Zhu Z, Jim C K W, Yu G, Li Q, Li Z, LiuY, Qin J, Tang B Z. Fluorescenceenhancements of benzene-cored luminophorsby restricted intramolecular rotations: AIE and AIEE effects [J]. Chemical Communication, 2007, 1:70-72.
[29] Hirano K, Minakata S, Komatsu M,Mizuguchi J. Intense blue luminescence of 3,4,6-triphenyl-alpha-pyrone in the solid stateand its electronic characterization [J]. The Journal of Physical Chemistry A,2002, 106:4868-4871.
[30] Shiraishi K, Kashiwabara T, Sanji T,Tanaka M. Aggregation-induced emission ofdendritic phosphole oxides [J]. New Journal of Chemistry,2009, 33: 1680-1684.
[31] 钱立军,佟斌,支俊格,杨帆,申进波, 石建兵,董宇平.含磷酰杂菲苯甲酸对苯二酯的聚集诱导发光增强性能及其在检测过渡金属离子中的应用[J].化学学报, 2006, 66: 1134-1138. Qian L J, Tong B, Zhi J G, Yang F, Shen J B, Shi J B, Dong Y P.Aggregation-induced emission enhancement of phosphaphenan threne-containing p-phenylene dibenzoate and its application to detecting transition metal ions[J]. Acta Chimica Sinica, 2006, 66: 1134-1138.
[32] Hu R, Lager E, Aguilar-Aguilar A, Liu J,Lam J W Y, Sung H H Y, Williams I D, ZhonY, Wong K S, Pena-Cabrera E, Tang B Z.Twisted intramolecular charge transfer andaggregation-induced emission of BODIPY derivatives [J]. The Journal of Physical Chemistry C, 2009, 113: 15845-15853.
[33] Qin A J, Lam J W Y, Mahtab F, Jim C K W, Tang L, Sun J Z, Sung H H Y, Williams I D, Tang B Z. Pyrazine Luminogens with "free" and "locked" phenyl rings: understanding of restriction of intramolecular rotation as a cause for aggregation-induced emission [J]. Applied Physics Letter, 2009, 94: 253308
[34] Chen M, Li L Z, Nie H, Tong J Q, Yan L L, Xu B, Sun J Z, Tian W J, Zhao Z J,Qin A J and Tang B Z. Tetraphenylpyrazine-based AIE gens: facilepreparation and tunable lightemission [J]. Chemical Science,2015,6: 1932-1937.
[35] Tracy H J, Mullin J L, Klooster W T.Enhanced photoluminescence from group 14 metalloles in aggregatedand solid solutions [J]. Inorganic Chemistry,2005, 44: 2003-2011.
[36] Xing Y J, Xu X Y, Wang F, Lu P. Optical properties of a series of tetraarylthiophenes [J]. Optical Materials, 2006, 29: 407-409.
[37] Deng S L, Chen T L, Chien W L, Hong J L. Aggregation-enhanced emission in fluorophores containing pyridine andtriphenylamine terminals: restricted molecular rotation andhydrogen-bond interaction [J]. Journal of Materials Chemistry C, 2014, 2: 651-659.
[38] Zhu Y, Rabindranath A R, Beyerlein T, Tieke B. Highly luminescent 1,4-diketo-3,6-diphenylpyrrolopyrrole-(DPP-)based conjugated polymers prepared upon suzuki coupling [J]. Macromolecules, 2007, 40: 6981-6989.
[39] Morales-Saavedra O G, Huerta G, Ortega-Martinez R, Fomina L. Linear and non-linear optical properties of 2,5-disubstituted pyrroles supported by a catalyst-free SiO₂ sonogel network [J]. Journal of Non-Crystalline Solids,2007, 353: 2557-2566.
[40] Alberola A, Ortega A G, Sádaba M L, Saudo C. Versatility of weinreb amides in the knorr pyrrole synthesis [J]. Tetrahedron, 1999, 55: 6555-6566.
[41] Jones R A, Been G P. The Chemistry of Pyrroles[M]. New York: Academic Press,1977. 50-54.
[42] Chiu P K, Lui K H, Maini P N, Sammes M P. Novel synthesis of 3H-pyrroles, and novel intermediates in the Paal-Knorr 1H-pyrrole synthesis:2-hydroxy-3,4-dihydro-2H-pyrrolesfrom 1,4-diketones and liquid ammonia [J]. Journal of the Chemical Society, Chemical Communications,1987: 109-110.
[43] Reisch J, Schulte K E.Pyrrol-derivate aus diacetylenen [J]. Angewandte Chemie, 1961, 73: 241-247.
[44] Huerta G, Fomina L, Rumsh L, Zolotukhin M G. New polymers with N-phenyl pyrrole fragments obtained by chemical modifications of diacetylene containing-polymers[J]. Polymer Bulletin, 2006, 57: 433-443.
[45] Feng X, Tong B, Shen J B, Shi J B, Han T Y, Chen L, Zhi J G, Lu P, Ma Y G, Dong Y P. Aggregation-induced emission enhancement of aryl-substituted pyrrole derivatives [J]. Journal of Physical Chemistry B, 2010, 114: 16731-16736.
[46] Han T Y, Feng X, Tong B, Shi J B, Chen L, Zhi J G, Dong Y P. A novel "'turn-on" fluorescent chemosensor for the selective detection of Al³⁺ based on aggregation-induced emission [J]. Chemical Communications, 2012, 48: 416-418.
[47] Shi X Y, Wang H, Han T Y, Feng X, Tong B, Shi J B, Zhi J G, Dong Y P. A highly sensitive, single selective, real-time and "turn-on" fluorescent sensor for Al³⁺ detection in aqueous media[J].Journal of Materials Chemistry, 2012, 22: 19296-19302.
[48] Hau F K, He X M, Lam W H, Yam V W W, Highly selective ion probe for Al³⁺ based on Au(Ⅰ)…Au(Ⅰ) interactions in a bis-alkynyl calixarene Au(Ⅰ) isocyanide scaffold [J]. Chemical Communications, 2011, 47: 8778-8780.
[49] Xie X J, Qin Y. A dual functional near infrared fluorescent probe based on the bodipy fluorophores for selective detection of copper and aluminum ions [J]. Sensors and Actuators B: Chemical, 2011, 156: 213-217.
[50] Han T Y, Feng X, Shi J B, Tong B, Dong Y F, Lam J W Y, Dong Y P, Tang B Z. DMF-induced emission of an aryl-substituted pyrrole derivative: a solid thermo-responsive material to detect temperature in a specific range [J]. Journal of Materials Chemistry C, 2013, 1: 7534-7539.