Two novel blue-emitting triazine-containing hyperbranched amides with donor-acceptor architecture were designed and synthesized via a one-pot polycondensation using 2,4,6-tris(4-carboxyphenyl)-1,3,5-triazine (H3TATB) and p-phenylenediamine as reaction materials. The prepared polymers were characterized using fourier transform infrared spectroscopy (FTIR), 1H–nuclear magnetic resonance (1H–NMR), and gel permeation chromatography (GPC) analyses. The two polymers are almost amorphous and are soluble in DMSO. Their solutions mainly emitted strong blue light (457–476 nm). The fluorescence quantum yields (QYs) in DMSO were calculated as 41% and 8% for P1–1 and P2–1, respectively. Density functional theory (DFT) calculations demonstrated that the highest occupied molecular orbit (HOMO) and lowest unoccupied molecular orbit (LUMO) were effectively separated with p-phenylenediamine as a donor unit and H3TATB as an acceptor unit. The effective HOMO−LUMO separation helps to induce intramolecular charge transfer from the HOMO to the LUMO. This results a relatively small energy gap between the singlet and triplet excited states, and as a consequence, these polymers are expected to harness both singlet and triplet excitons for light emission, leading to high external electroluminescence efficiency. The merits of the two polymers are organo-solubility and high fluorescence quantum yield. Both P1–1 and P2–1 are sensitive fluorescent indicators for Fe3+ ion. They are potential useful in the area of blue light emitting, display and fluorescent chemosensor for Fe3+ ion.
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The author thanks the Scientific research project fund of Shaanxi Province Key Laboratory of Phytochemistry of China (14JS006), the Doctoral research start-up project fund of Baoji University of Arts and Sciences (ZK2017032), the Nature science project fund of Shaanxi Educational Committee of China (16JK1050) and the project fund of Baoji University of Arts and Sciences (ZK15049) for the support.
Sun J, Wang H, Yang T, Zhang X, Li J, Zhang T, Wu Y, Chen W, Wong W-Y, Xu B (2016) Design, synthesis and properties of triple-color hyperbranched polymers derived from poly(9,9-dioctylfluorene) with phosphorescent core tris(1-phenylisoquinoline)iridium(III). Dyes Pigments 125:339–347. https://doi.org/10.1016/j.dyepig.2015.10.043.CrossRefGoogle Scholar
Shizu K, Noda H, Tanaka H, Taneda M, Uejima M, Sato T, Tanaka K, Kaji H, Adachi C (2015) Highly efficient blue electroluminescence using delayed-fluorescence emitters with large overlap density between luminescent and ground states. J Phys Chem C 119:26283–26289. https://doi.org/10.1021/acs.jpcc.5b07798.CrossRefGoogle Scholar
Elim HI, Anandakathir R, Jakubiak R, Chiang LY, Ji W, Tan LS (2007) Large concentration-dependent nonlinear optical responses of starburst diphenylaminofluorenocarbonyl methanofullerene pentads. J Mater Chem 17:1826–1838. https://doi.org/10.1039/B615697ECrossRefGoogle Scholar
Matsushima T, Takamori M, Miyashita Y, Honma Y, Tanaka T, Aihara H, murata H (2010) High electron mobility layers of triazines for improving driving voltages, power conversion efficiencies, and operational stability of organic light-emitting diodes. Org Electron 11:16–22. https://doi.org/10.1016/j.orgel.2009.09.016CrossRefGoogle Scholar
Wang Q, Wallace JU, Lee TYH, Ou JJ, Tsai YT, Huang YH, Wu CC, Rothberg LJ, Chen SH (2013) Evaluation of propylene-, meta-, and para-linked triazine and tert-butyltriphenylamine as bipolar hosts for phosphorescent organic light-emitting diodes. J Mater Chem C 1:2224–2232. https://doi.org/10.1039/C3TC00588GCrossRefGoogle Scholar
Liu XK, Zheng CJ, Xiao J, Ye J, Liu CL, Wang SD, Zhao WM, Zhang XH (2012) Novel bipolar host materials based on 1,3,5-triazine derivatives for highly efficient phosphorescent OLEDs with extremely low efficiency roll-off. Phys Chem Chem Phys 14:14255–14261. https://doi.org/10.1039/c2cp41542aCrossRefGoogle Scholar
Chang CH, Kuo MC, Lin WC, Chen YT, Wong KT, Chou SH, Ejabul M, Raymond CK, Sean X, Tetsuya N, Chihaya A (2012) A dicarbazole–triazine hybrid bipolar host material for highly efficient green phosphorescent OLEDs. J Mater Chem 22:3832. https://doi.org/10.1039/C2JM14686J.CrossRefGoogle Scholar
Volz D, Wallesch M, Flechon C, Danz M, Verma A, Navarro JM, Zink DM, Bräse S, Baumann T (2015) From iridium and platinum to copper and carbon: new avenues for more sustainability in organic light-emitting diodes. Green Chem 17:1988–2011. https://doi.org/10.1039/C4GC02195ACrossRefGoogle Scholar
Liu JZ, Zhong YC, Lu P, Hong YN, Lam JWY, Faisal M, Yu Y, Wong KS, Tang BZ (2010) A superamplification effect in the detection of explosives by a fluorescent hyperbranched poly(silylenephenylene) with aggregation-enhanced emission characteristics. Polym Chem 1:426–429. https://doi.org/10.1039/C0PY00046ACrossRefGoogle Scholar