Syntheses, characterizations, and properties of 1,4-phenylene and 4,4′-biphenylene bridged BOBPY dimers

被引：1
|
作者：
Wang, Jun [1 ,2 ]
Zuo, Huiquan [2 ]
Wu, Qinghua [3 ]
Hao, Erhong [2 ]
Jiao, Lijuan [2 ]
机构：
[1] Hefei Normal Univ, Dept Chem & Chem Engn, Anhui Engn Lab Med & Food Homologous Nat Resources, Hefei, Peoples R China
[2] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Funct Mol Solids, Anhui Lab Mol Based Mat,Minist Educ, Wuhu, Peoples R China
[3] Anhui Univ Chinese Med, Sch Pharm, Hefei, Peoples R China
来源：
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES | 2023年 / 27卷 / 01期
关键词：
BOBPY; dimer; bridged; solvent-dependent; photostable; TRIPLET EXCITED-STATE; LARGE STOKES SHIFT; ONE-POT SYNTHESIS; BODIPY DYES; ENERGY-TRANSFER; FUSED BODIPY; DEHYDROGENATIVE STRATEGY; PHOTOPHYSICAL PROPERTIES; SYMMETRY-BREAKING; FLUORESCENCE;
D O I：
10.1142/S1088424622500936
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Two novel phenylenes (1,4-phenylene and 4,4'-biphenylene) bridged dimeric BOBPY (Boron complexed N2O-type benzopyrromethenes) were designed and synthesized from the one-pot condensation of pyrrole with formylisoindole and subsequent complexation with diboronic acid. These novel dyes were fully characterized by NMR spectroscopy, HRMS, absorption and fluorescence emission spectroscopy, and cyclic voltammetry. These resulting BOBPY dimers are highly photostable and show intense absorption and emission in the region of 618 to 644 nm with high absorption coefficients and solvent-dependent fluorescence quantum yields. The electronic interactions between BOBPY units are related with length of the linker. And the dimer with short 1,4-phenylene linker was more sensitive to the polarity of the solvents than that of the other dimer, suggesting that the short linkage allowed stronger electronic communication between the two BOBPY units.
引用
收藏
页码：304 / 313
页数：10
相关论文
共 50 条
  • [41] Preparation and Characterization of Singlehanded Helical Carbonaceous Nanofibers using 1,4-Phenylene Bridged Polybissilsesquioxanes
    肖泽丽
    GUO Yongmin
    李宝宗
    LI Yi
    Journal of Wuhan University of Technology(Materials Science), 2016, 31 (05) : 1149 - 1154
  • [42] ELECTRICAL-PROPERTIES OF POLY(1,4-PHENYLENE VINYLENE-CO-2,5-DIMETHOXY-1,4-PHENYLENE VINYLENE)S AND POLY(1,4-PHENYLENE VINYLENE-CO-2,5-THIENYLENE VINYLENE)S
    SHIM, HK
    KIM, SK
    JIN, JI
    KIM, KH
    PARK, YW
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1990, 11 (01) : 11 - 15
  • [43] A New Strategy for Synthesis of Novel 1, 4-Phenylene Bridged Bis-Hetero Cyclic Compounds
    Hassaneen, Hamdi M.
    Shawali, Ahmad S.
    El Agaty, Lamiaa M.
    LETTERS IN ORGANIC CHEMISTRY, 2016, 13 (07) : 504 - 513
  • [44] Synthesis, Crystal Structures and Luminescent Properties of Zn(II)/Cd(II) Metal-Organic Frameworks Constructed by 1,4-Benzenedicarboxylic Acid and 4,4′-(2,5-Difluoro-1,4-phenylene)dipyridine
    Yang, Yi
    Qi, Xiu-Xiu
    Chen, Hao-Ran
    Wang, Xi-Yao
    Yang, Xiao-Lin
    Tu, Yu-Yu
    Zhou, Tiantian
    Jiang, Tianyu
    Wang, Fei
    Chen, Ziying
    Ju, Yi-Chun
    JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2020, 30 (11) : 4289 - 4296
  • [45] Syntheses, characterizations and properties of boronoalkylalkoxycalix[4]arenes
    Lu, K
    Wu, YJ
    Wang, HX
    Zhou, ZX
    POLYHEDRON, 1999, 18 (8-9) : 1153 - 1158
  • [46] Syntheses, Structures and Fluorescent Properties of Copper(II) and Manganese(II) Helical Complexes Bridged by 4,4′-Dipyridylsulfide
    Li Jun-Xia
    Du Zhong-Xiang
    CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2012, 31 (06) : 877 - 883
  • [47] Molecular and crystal structure of 4,5,4',5'-tetrahydro-2,2'-(1,4-phenylene)bisoxazoline
    Pankratov, VA
    Mitina, LM
    Doroshenko, YE
    Yaskevich, VV
    Khrustalev, VN
    Lindeman, SV
    Struchkov, YT
    RUSSIAN CHEMICAL BULLETIN, 1996, 45 (10) : 2378 - 2379
  • [48] Mesomorphic and ion conducting properties of dialkyl(1,4-phenylene) diimidazolium salts
    Noujeim, Nadim
    Samsam, Salim
    Eberlin, Ludovic
    Sanon, Samantha H.
    Rochefort, Dominic
    Schmitzer, Andreea R.
    SOFT MATTER, 2012, 8 (42) : 10914 - 10920
  • [49] Design, synthesis, antimicrobial and cytotoxicity study on human colorectal carcinoma cell line of new 4,4′-(1,4-phenylene)bis(pyrimidin-2-amine) derivatives
    Sanjiv Kumar
    Siong Meng Lim
    Kalavathy Ramasamy
    Vasudevan Mani
    Syed Adnan Ali Shah
    Balasubramanian Narasimhan
    Chemistry Central Journal, 12
  • [50] Transformation kinetics of liquid-crystallines based on 1,4-phenylene 4-n-Alkylbenzoate-4-Allyloxybenzoate by DSC
    Bo, ZL
    Shen, YP
    INTERNATIONAL JOURNAL OF CHEMICAL KINETICS, 1997, 29 (05) : 317 - 321
12345