Abstract
A series of π-conjugated compounds ending with 9,9-diethyl-1-phenyl-1,9-dihydrofluoreno[2,3-d]imidazole were conveniently synthesized by condensation of the key intermediate 9,9-diethyl-N2-phenyl-9H-fluorene-2,3-diamine with the corresponding symmetric aryl phthalaldehydes under very mild conditions. The structures of these compounds were confirmed by 1H NMR, 13C NMR, and HRMS. Their UV-Vis spectroscopy data, fluorescent spectroscopy data, and further details of the electronic properties from cyclic voltammetry measurements and theoretical calculations were studied. Most compounds possess good fluorescence-emitting ability with quantum yield of fluorescence values in the region of 0.36–0.92 and display emission within 449–513 nm depending on the molecular nature.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Ramkia NK, Venkateshab G, Sathiyan, et al. A Comprehensive Review on the Reasons behind Low Power Conversion Efficiency of Dibenzo Derivatives Based Donors in Bulk Heterojunction Organic Solar Cells[J]. Org. Electron., 2019, 73: 182–204
Shawkat MA, Ho CL, Wong WY, et al. Intrachain Electron and Energy Transfers in Metal Diynes and Polyynes of Group 10–11 Transition Elements Containing Various Carbazole and Fluorene Hybrids[J]. Macromolecules, 2009, 42: 6 902–6 916
Vasilopoulou M, Palilis LC, Botsialas A, et al. Flexible Organic Light Emitting Diodes (OLEDs) Based on a Blue Emitting Polyfluorene[J]. Phys. Status. Solidi. A, 2008, 5: 3 658–3 662
Hussein EM, Guesmi NE, Majid TK, et al. Synthesis and Photophysical Properties of Benzimidazoles Grafted Pyrazole-containing Pyrene or Fluorene Moiety: A Combined Spectroscopic and Computational Study[J]. J. Photoch. Photobio. A, 2021, 419: 113 456
Zhen CG, Chen ZK, Liu QD, et al. Fluorene-Based Oligomers for Highly Efficient and Stable Organic Blue-Light-Emitting Diodes[J]. Adv. Mater, 2009, 21: 2 425–2 429
Seidel P, Seichter W, Schwarzer A, et al. Fluorene Derivatives Bearing Two to Seven Phthalimidomethyl Groups: Syntheses, Crystal Structures and Conversion to Amines[J]. Eur J. Org. Chem., 2021, 2021: 2 901–2 914
Zhu M, Ye T, Li CG, et al. Efficient Solution-Processed Nondoped Deep-Blue Organic Light-Emitting Diodes Based on Fluorene-Bridged Anthracene Derivatives Appended with Charge Transport Moieties[J]. J. Phys. Chem. C, 2011, 115: 17 965–17 972
Han Y, Bai L, Yin C, et al. Solution-Processed Diarylfluorene Derivatives for Violet-blue Amplified Spontaneous Emission and Electroluminescence[J]. J.Mater Chem. C, 2017, 5: 9 903–9 910
Thomas KR, Venkateswararao A, Joseph A, et al. Polarity Tuning of Fluorene Derivatives by Chromophores to Achieve Efficient Blue Electroluminescent Materials[J]. Org. Electron., 2019, 64: 266–273
Sprick RS, Bai Y, Guilbert AA. Photocatalytic Hydrogen Evolution from Water Using Fluorene and Dibenzothiophene Sulfone-Conjugated Microporous and Linear Polymers[J]. Chem. Mater., 2019, 31: 305–313
Ma G, Zhao H, Wang J, et al. Studies of Fluorine Auxochrome in C9-Fluorenyl Anthracenes on Optoelectronic Property for Blue Electroluminescent Materials[J]. Dyes. Pigm., 2018, 158: 420–427
Ma H, Li Y, Wu S, et al. Photo- and Electro-luminescent Properties of 2,7-Disubstituted Spiro[fluorene-9,9′-xanthene] Derivatives Containing Imidazole-derived Moieties[J]. New J. Chem., 2021, 45: 19 381–19 390
Pham HD, Escrig LG, Feron K, et al. Boosting Inverted Perovskite Solar Cell Performance by Using 9,9-Bis(4-diphenylaminophenyl) fluorene Functionalized with Triphenylamine as a Dopant-free Hole Transporting Material[J]. J. Mater. Chem. A, 2019, 7(20): 12 507–12 517
Liu Y, Lin J, Xie H, et al. Synthesis and Crystal Structure of Highly Strained Cyclofluorene: Green Emitting Fluorophores[J]. Org. Lett., 2016, 18: 172–175
Sun W, Zhou N, Xiao Y, et al. Novel Carbazolyl-substituted Spiro [acridine-9,9′-fluorene] Derivatives as Deep-blue Emitting Materials for OLED Applications[J]. Dyes Pig., 2018,154: 30–37
Tang F, Peng J, Liu R, et al. A Sky-blue Fluorescent Small Molecule for Non-doped OLED Using Solution-processing[J]. RSC. Adv., 2015, 5: 71 419–71 424
Chen X, Zhuang X, Wang Z, et al. A Multifunctional Bipolar Host Material Based on Phenanthroimidazole for Efficient Green and Red PhOLEDs with Low Turn-on Voltage[J]. Org. Electron., 2019, 69: 85–91
Thiery S, Heinrich B, Donnio B, et al. Modulation of the Electronic and Mesomorphic Properties of Alkynyl-Spirobifluorene Compounds as a Function of the Substitution Pattern[J]. J. Phys. Chem. C, 2015, 119: 10 564–10 575
Jang SE, Joo CW, Yook KS, et al. Thermally Stable Fluorescent Blue Organic Light-emitting Diodes Using Spirobifluorene Based Anthracene Host Materials with Different Substitution Position[J]. Synth. Met., 2010, 160: 1 184–1 188
Wang W, Zhan C, Xiao SQ. Isomeric Fluorene-based Heteroundecenes with Different Side Chains Anchoring Positions for Small Molecule Acceptors[J]. J. Wuhan Univ. Technol., 2022, 1: 136–147
Wang T, Zhao S, Zhang W, et al. Synthesis, X-ray Crystal Structure, and Optical Properties of Novel 9,9-Diethyl-1,2-diaryl-1,9-dihydrofluoreno[2,3-d]imidazoles[J]. Monatsh. Chem., 2016, 147: 1 991–1 999
Chen L, Wang X, Zhang C, et al. n-Conjugated Twin Molecules Based on 9,9-Diethyl- 1-phenyl- 1,9-dihydrofluoreno[2,3-d]imidazole Module: Synthesis, Characterization, and Electroluminescence Properties[J]. Monatsh. Chem., 2020, 151: 917–924
Wang X, Zhang C, Wang T, et al. Synthesis and Application of a Novel 9,9-Diethyl-1,2-diaryl-1,9-dihydrofluoreno[2,3-d]imidazole for Blue Organic Light Emitting Diode[J]. Chin. Chem. Lett., 2020, 31: 64–66
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
All authors declare that there are no competing interests.
Additional information
Funded by the Natural Science Foundation of Shanghai City (No. 19ZR1419700)
Rights and permissions
About this article
Cite this article
Li, S., Wang, T., Tan, Q. et al. Synthesis and Characterization of 9,9-diethyl-1-phenyl-1,9-dihydrofluoreno[2,3-d]imidazole-ended Fluorophores. J. Wuhan Univ. Technol.-Mat. Sci. Edit. 38, 1484–1488 (2023). https://doi.org/10.1007/s11595-023-2845-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11595-023-2845-7