Study on Synthesis and Properties of New Indeno[2,1-b]fluorene-5,7-dione Derivatives

doi:10.6023/cjoc202412016

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2444-2450.DOI: 10.6023/cjoc202412016 Previous Articles Next Articles

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新型茚并芴-5,7-二酮衍生物的合成与性质研究

王静^*(), 陈宇讯, 姜静静

商丘师范学院化学化工学院河南商丘 476000

收稿日期:2025-01-19 修回日期:2025-02-08 发布日期:2025-02-27
基金资助:
国家自然科学基金(21302120)

Study on Synthesis and Properties of New Indeno[2,1-b]fluorene-5,7-dione Derivatives

Jing Wang^*(), Yuxun Chen, Jingjing Jiang

College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000

Received:2025-01-19 Revised:2025-02-08 Published:2025-02-27
Contact: *E-mail: wj2150@yeah.net
Supported by:
National Natural Science Foundation of China(21302120)

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Abstract

Indeno[2,1-b]fluorene-5,7-dione derivatives modified by different alkyl chains were designed and synthesized. The introduced alkyl chains not only improved the solubility of the compounds, which facilitated the separation and purification to characterize their structures, but also regulated the properties and then proved the chance to investigate the relationship between the structure and property. It was found that the solubility, thermal and optical stability of the new compounds were good. Compounds 5b~5d have increased electronegativities because of the lowest unoccupied molecular orbital (LUMO) energies (≤－3.4 eV). The crystalline structure of 3,9-ditert-butylindeno]2,1-b]fluorene-5,7-dione (5d) shows that it forms a nearly planar five-membered ring skeleton and slipped face-to-face π-stacks with a layer space of 0.3541 nm, and the direction of carbonyl groups in adjacent deposits is opposite. The molecular packing could facilitate carrier transport. This article provides some guidance for the design of organic functional molecules, and provides new materials source for field effect transistors.

Key words: indeno[2,1-b]fluorine-5,7-dione, organic functional material, Suzuki coupling reaction

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Jing Wang, Yuxun Chen, Jingjing Jiang. Study on Synthesis and Properties of New Indeno[2,1-b]fluorene-5,7-dione Derivatives[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2444-2450.

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Fig. & Tab. 8

Scheme 1. Synthetic route to compounds 5a~5d

Figure 1. Normalized UV-vis absorption spectra in DCM of 5a~5d (10 μmol/L)

Compd.	λ_abs/nm	E_g^a/eV	λ_em/nm	T_dec/℃	E1 red/V	E2 red/V	E3 red/V	Eonset red/V	E_HOMO^b/eV	E_LUMO^c/eV
5a	440, 405, 385, 320, 305, 282	2.61	544	418
5b	485, 450, 413, 390, 338, 325, 282	2.43	557	413	－1.32	－1.64	—	－0.97	－5.86	－3.43
5c	485, 450, 413, 390, 338, 325, 282	2.42	558	416	－1.23	－1.55	－1.74	－0.92	－5.90	－3.48
5d	485, 450, 410, 389, 338, 325, 282	2.43	556	420	－1.08	－1.45	－1.65	－0.91	－5.92	－3.49

Table 1. Optical data, decomposition temperatures and electrochemical properties for compounds 5a~5d

Figure 2. Photo-stability of 5a~5d monitored through decrease in their absorption upon exposure to ambient light and air at 18 ℃

Figure 3. Normalized fluorescence spectra of 5a~5d (10 μmol/L) recorded in DCM Excitation wavelength of 5a~5d: 350 nm, slit width 5 nm.

Figure 4. Cyclic voltammograms of 5b~5d (0.001 mol/L)

Figure 5. TGA plots of 5a~5d with a heating rate of 10 ℃• min－1 under N2

Figure 6. X-ray crystal structure of 5d Red spheres depict O atoms and gray spheres represent C; Hydrogen atoms have been omitted for clarity in packing.

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新型茚并芴-5,7-二酮衍生物的合成与性质研究

Study on Synthesis and Properties of New Indeno[2,1-b]fluorene-5,7-dione Derivatives

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References 25

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