|Synthesis of Aryl-substituted Pyrrole Derivatives with Tunable Emissive Behaviors
|GAO Yu, LIU Guogang, SHI Jianbing, DONG Yuping
|Beijing Key Laboratory of Construction Tailorable Advanced Functional Materials and Green Applications, School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, P. R. China
|  Jia Y, Zhang Y T, Fan S G, Wu S, Zhan X M, Wang S R, Li X G. A novel bipolar carbazole/phenanthroimidazole derivative for high efficiency nondoped deep-blue organic light-emitting diodes[J]. Organic Electronics, 2019,64:259-265.
 Chen Q, Liu D P, Zhu J H, Han B H. Mesoporous conjugated polycarbazole with high porosity via structure tuning[J]. Macromolecules, 2014,47(17):5926-5931.
 Yang W, Chen Y, Jiang W, Ban X, Huang B, Dai Y, Sun Y. A carbazole-based dendritic host material for efficient solution-processed blue phosphorescent OLEDs[J]. Dyes and Pigments, 2013,97(2):286-290.
 Zhang F, Zhou C, Yan J. New progress of researches in carbazole compounds[J]. Chinese Journal of Organic Chemistry, 2010,30(6):783-796.
 He Y, Feng R, Yi Y, Liu Z. Recent progress in the research of borondipyrromethene-based fluorescent ion chemosensor[J]. Chinese Journal of Organic Chemistry, 2014,34(11):2236-2248.
 Fan G, Yang L, Chen Z. Water-soluble BODIPY and aza-BODIPY dyes:synthetic progress and applications[J]. Frontiers of Chemical Science and Engineering, 2014,8(4):405-417.
 Zhao Q, Yin C X, Kang J, Wen Y, Huo F J. A viscosity sensitive azide-pyridine BODIPY-based fluorescent dye for imaging of hydrogen sulfide in living cells[J]. Dyes and Pigments, 2018,159:166-172.
 Tanaka T, Osuka A. Conjugated porphyrin arrays:synthesis, properties and applications for functional materials[J]. Chemical Society Reviews, 2015,44(4):943-69.
 Buimaga-Iarinca L, Morari C. Charge transport pathways in metal porphyrin as interplay between long and short range scattering processes[J]. Nanotechnology, 2019,30(4):045204.
 Berlicka A, Dutka P, Szterenberg L, Latos-Grazynski L. Towards true carbaporphyrinoids:synthesis of 21-carba-23-thiaporphyrin[J]. Angewandte Chemie-International Edition, 2014,53(19):4885-4889.
 Tagawa K, Mori S, Okujima T, Takase M, Uno H. Protonation behavior of thiaporphyrin and thiabenzoporphyrin[J]. Tetrahedron, 2017,73(6):794-801.
 Ding Y, Tang Y, Zhu W, Xie Y. Fluorescent and colorimetric ion probes based on conjugated oligopyrroles[J]. Chemical Society Reviews, 2015,44(5):1101-1112.
 Degirmenci A, Iskenderkaptanoglu D, Algi F. A novel turn-off fluorescent Pb(Ⅱ) probe based on 2,5-di(thien-2-yl) pyrrole with a pendant crown ether[J]. Tetrahedron Letters, 2015,56(4):602-607.
 Li C, Liu C, Li Y, Zhu X, Wang Z. Facile synthesis of a pyrrole-fused dibenzo a,e pentalene and its application as a new extended, ladder-type fused aromatic system[J]. Chemical Communications, 2015,51(4):693-696.
 Liu G, Chen D, Kong L, Shi J B, Tong B, Zhi J G, Feng X, Dong Y P. Red fluorescent luminogen from pyrrole derivatives with aggregation-enhanced emission for cell membrane imaging[J]. Chemical Communications, 2015,51(40):8555-8558.
 Han T, 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(45):7534-7539.
 Dong L C, Shang G J, Shi J B, Zhi J G, Tong B, Dong Y P. Effect of substituent position on the photophysical properties of triphenylpyrrole isomers[J]. Journal of Physical Chemistry C, 2017,121(21):11658-64.
 Lei Y X, Liu Q W, Dong L C, Cai Z X, Shi J B, Zhi J G, Tong B, Dong Y P. The dual-state luminescent mechanism of 2,3,4,5-tetraphenyl-1H-pyrrole[J]. Chemistry-A European Journal, 2018,24(53):14269-14274.
 Lei Y X, Lai Y Y, Dong L C, Shang G J, Cai Z X, Shi J B, Zhi J G, Li P F, Huang X B, Tong B, Dong Y P. The synergistic effect between triphenylpyrrole isomers as donors, linking groups, and acceptors on the fluorescence properties of D-A compounds in the solid state[J]. Chemistry-A European Journal, 2018,24(2):434-442.
 Chen D D, Wang H, Liu P, Song L L, Shi J B, Tong B, Dong Y P. The application of CO2-sensitive AIEgen in studying the synergistic effect of stromal cells and tumor cells in a heterocellular system[J]. Analytica Chimica Acta, 2018,1001:151-157.
 Chen D D, Dong L C, Jiang S, Li W Y, Shi J B, Feng X, Zhi J G, Tong B, Li M, Zheng Q C, Dong Y P. Two-step separation-free quantitative detection of HSA and FIB in human blood plasma by a pentaphenylpyyrrole derivative with aggregation-enhanced emission properties[J]. Sensors and Actuators B-Chemical, 2018,255:854-861.
 Liu P, Li W Y, Guo S, Xu D R, Wang M N, Shi J B, Cai Z X, Tong B, Dong Y P. Application of a novel "turn-on" fluorescent material to the detection of aluminum ion in blood serum[J]. Acs Applied Materials & Interfaces, 2018,10(28):23667-23673.
 Chen D D, Wang H, Dong L C, Liu P, Zhang Y H, Shi J B, Feng X, Zhi J G, Tong B, Dong Y P. The fluorescent bioprobe with aggregation-induced emission features for monitoring to carbon dioxide generation rate in single living cell and early identification of cancer cells[J]. Biomaterials, 2016,103:67-74.
 Liang J, Tang B Z, Liu B. Specific light-up bioprobes based on AIEgen conjugates[J]. Chemical Society Reviews, 2015,44(10):2798-811.
 Kwok R T K, Leung C W T, Lam J W Y, Tang B Z. Biosensing by luminogens with aggregation-induced emission characteristics[J]. Chemical Society Reviews, 2015,44(13):4228-4238.
 Zhao Z J, He B R, Tang B Z. Aggregation-induced emission of siloles[J]. Chemical Science, 2015,6:5347-5365.
 Zhuang Z Y, Bu F, Luo W W, Peng H R, Chen S M, Hu R R, Qin A J, Zhao Z J, Tang B Z. Steric, conjugation and electronic impacts on the photoluminescence and electroluminescence properties of luminogens based on phosphindole oxide[J]. Journal of Materials Chemistry C, 2017,5:1836-1842.
 Shen P C, Zhuang Z Y, Zhao Z J, Tang B Z. AIEgens based on main group heterocycles[J]. Journal of Materials Chemistry C, 2018,6:11835-11852.
 Zhang W, Kwok R T K, Chen Y, Chen S, Zhao E, Yu C Y Y, Lam J W Y, Zheng Q, Tang B Z. Real-time monitoring of the mitophagy process by a photostable fluorescent mitochondrion-specific bioprobe with AIE characteristics[J]. Chemical Communications, 2015,51(43):9022-9025.
 Yuan Y, Zhang C J, Liu B. A platinum prodrug conjugated with a photosensitizer with aggregation-induced emission (AIE) characteristics for drug activation monitoring and combinatorial photodynamic-chemotherapy against cisplatin resistant cancer cells[J]. Chemical Communications, 2015,51(41):8626-8629.
 Ni Y, Wu J. Far-red and near infrared BODIPY dyes:synthesis and applications for fluorescent pH probes and bio-imaging[J]. Organic & Biomolecular Chemistry, 2014,12(23):3774-3791.
 Vegesna G K, Janjanam J, Bi J, Luo F T, Zhang J, Olds C, Tiwari A, Liu H. pH-activatable near-infrared fluorescent probes for detection of lysosomal pH inside living cells[J]. Journal of Materials Chemistry B, 2014,2(28):4500-4508.
 Ning Z, Chen Z, Zhang Q, Yan Y, Qian S, Cao Y, Tian H. Aggregation-induced emission (AIE)-active starburst triarylamine fluorophores as potential non-doped red emitters for organic light-emitting diodes and Cl-2 gas chemodosimeter[J]. Advanced Functional Materials, 2007,17(18):3799-3807.
 Zhang Z, Edkins R M, Nitsch J, Fucke K, Eichhorn A, Steffen A, Wang Y, Marder T B. D-pi-A triarylboron compounds with tunable push-pull character achieved by modification of both the donor and acceptor moieties[J]. Chemistry-A European Journal, 2015,21(1):177-190.
 Feng G, Liu J, Zhang R, Liu B. Cell imaging using red fluorescent light-up probes based on an environment-sensitive fluorogen with intramolecular charge transfer characteristics[J]. Chemical Communications, 2014,50(67):9497-9500.
 Shimada M, Yamanoi Y, Matsushita T, Kondo T, Nishibori E, Hatakeyama A, Sugimoto K, Nishihara H. Optical properties of disilane-bridged donor acceptor architectures:strong effect of substituents on fluorescence and nonlinear optical properties[J]. Journal of the American Chemical Society, 2015,137(3):1024-1027.
 Ni W, Wan X, Li M, Wang Y, Chen Y. A-D-A small molecules for solution-processed organic photovoltaic cells[J]. Chemical Communications, 2015,51(24):4936-4950.
 Gupta A, Ali A, Bilic A, Singh T B, Evans R A. Symmetrical and unsymmetrical donor-acceptor-donor organic dyes:design, synthesis and characterization. Engineering panchromic absorbance[J]. Dyes and Pigments, 2014,108:15-23.
 Das P, Butcher R J, Mukhopadhyay C. Zinc titanate nanopowder:an advanced nanotechnology based recyclable heterogeneous catalyst for the one-pot selective synthesis of self-aggregated low-molecular mass acceptor-donor-acceptor-acceptor systems and acceptor-donor-acceptor triads[J]. Green Chemistry, 2012,14(5):1376-1387.
 Yang J, Li J, Hao P, Qiu F, Liu M, Zhang Q, Shi D. Synthesis, optical properties of multi donor-acceptor substituted AIE pyridine derivatives dyes and application for Au3+ detection in aqueous solution[J]. Dyes and Pigments, 2015,116:97-105.
 Zhao L, Liu C F, Xu W D, Jiang Y, Lai W Y, Huang W. Donor-acceptor star-shaped conjugated macroelectrolytes:synthesis, light-harvesting properties, and self-assembly-induced forster resonance energy transfer[J]. Journal of Physical Chemistry B, 2015,119(22):6730-6739.
 Zhang J, Zhao C, Liu H, Lv Y, Liu R, Zhang S, Chen H, Zhang G, Tian Z. Solvatochromic fluorescence emission of an anthranol derivative without typical donor-acceptor structure:an experimental and theoretical study[J]. Journal of Physical Chemistry C, 2015,119(5):2761-2769.
 Bu F, Wang E, Peng Q, Hu R, Qin A, Zhao Z, Tang B Z. Structural and theoretical insights into the AIE attributes of phosphindole oxide:the balance between rigidity and flexibility[J]. Chemistry-A European Journal, 2015,21(11):4440-4449.
 Dong Y F, Wang W, Zhong C, Shi J B, Tong B, Feng X, Zhi J, Dong Y P. Investigating the effects of side chain length on the AIE properties of water-soluble TPE derivatives[J]. Tetrahedron Letters, 2014,55(8):1496-1500.
||JIA Zeli, GAO Jianfeng, LI Xubing, FENG Ke, CHEN Bin, YANG Qingzheng, CHEN Yuzhe, TONG Zhenhe, WU Lizhu. The Construction and Photophysical Studies of Iodinated Bodipy Based Supramolecular Polymer[J]. Imaging Science and Photochemistry, 2017, 35(4): 516-525.