Color-tunable Fluorescent Ink Based on Single Benzene Fluorophore

Hai-xiang MAO; Biao WANG; Bin-bin DING; Min-jie GUO; Zhi FAN; Sheng-hua LI; Jing CUI

doi:10.37188/CJL.20200280

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Color-tunable Fluorescent Ink Based on Single Benzene Fluorophore

Synthesis and Properties of Materials | 更新时间：2021-01-12

- Color-tunable Fluorescent Ink Based on Single Benzene Fluorophore
- Chinese Journal of Luminescence Vol. 42, Issue 1, Pages: 44-52(2021)
- 作者机构：
  
  1.天津科技大学化工与材料学院, 天津 300457
  2.中国石化上海石油化工研究院, 上海 201208
- 作者简介：
- 基金信息：
  
  National Natural Science Foundation of China;Scientific Research Project of Tianjin Educational Committee;National undergraduate innovation and entrepreneurship training program
- DOI：10.37188/CJL.20200280
  CLC： O482.31
- Published：2021-1，
  
  Received：18 September 2020，
  
  Accepted：27 October 2020
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Hai-xiang MAO, Biao WANG, Bin-bin DING, et al. Color-tunable Fluorescent Ink Based on Single Benzene Fluorophore. [J]. Chinese Journal of Luminescence 42(1):44-52(2021)
DOI：

Hai-xiang MAO, Biao WANG, Bin-bin DING, et al. Color-tunable Fluorescent Ink Based on Single Benzene Fluorophore. [J]. Chinese Journal of Luminescence 42(1):44-52(2021) DOI： 10.37188/CJL.20200280.

摘要

以丁二酸二丁酯为原料，经过缩合、氨化、芳构化合成了单苯环荧光化合物2，5-二氨基-1，4-苯二甲酸丁酯

。溶液中化合物

的最大荧光发射峰变化范围为60 nm，即从正己烷中的514 nm到乙二醇中的574 nm。化合物

在固态下经紫外光照射可发出黄色荧光，其最大发射波长为558 nm，荧光量子产率（

）为0.28。采用氯甲酸-2，2，2-三氯乙酯（TrocCl）将化合物

的氨基酰化可得到单酰胺化产物化合物

，固态下可发出绿色荧光，其最大荧光发射峰位于493 nm，

为0.13；进一步酰化可得到双酰胺化产物化合物

，固态下可发出蓝色荧光，其最大荧光发射波长467 nm，

为0.79。这一过程可以在本色纸上原位完成，进而实现荧光三色转变。即将化合物

溶液书写于纸张上可获得黄色荧光字样，在其上涂写不同浓度的TrocCl溶液可将纸张上的化合物

转化为化合物

和

，从而使字体的发光颜色变为绿色和蓝色。

Abstract

The single benzene fluorophore dibutyl-2

5-diaminoterephthalate

was synthesized by claisen condensation of dibutyl succinate followed by amination and aromatization. The maximum emission peaks of compound

are ranged from 514 nm in n-Hexane to 574 nm in glycol

spanning 60 nm. Compound

displays efficient yellow emissions in solid-state(the emission maxima

=558 nm

fluorescence quantum yield

=0.28). The acylation of amino group in compound

by 2

2-Trichloroethyl chloroformate(TrocCl) was led tomonoamide compound

which gives green emissions in solid-state(

=493 nm

=0.13); and further acylation led to diamide compound

which gives blue emissions in solid-state(

=467 nm

=0.79). Those trichromatic fluorescent transformation also can be achieved on unbleached papers. As a result of the acylation of compound

on paper

the emission color can be changed from yellow to green and blue after writing different concentration of colorless TrocCl solution on the top of fluorescent

characters

which makes it possible to apply widely as color-tunable fluorescent ink.

关键词

固态荧光变色调控二氨基对苯二甲酸酯溶致变色

Keywords

solid-state fluorescencecolour-tunablediaminoterephthalatesolvatochromism

references

LIU J H, YANG Z X, YE B Q, et al.. A review of stability-enhanced luminescent materials:fabrication and optoelectronic applications[J].J. Mater. Chem. C, 2019, 7(17):4934-4955.

GRIMSDALE A C, CHAN K L, MARTIN R E, et al.. Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices[J].Chem. Rev., 2009, 109(3):897-1091.

MULLEN K, SCHERF U. Organic Light-emitting Devices:Synthesis, Properties and Applications [M]. Weinheim:Wiley-VCH, 2006.

娄庆, 曲松楠.基于超级碳点的水致荧光"纳米炸弹"[J].中国光学, 2015, 8(1):91-98.

LOU Q, QU S N. Water triggered luminescent "nano-bombs" based on supra-carbon-nanodots[J].Chin. Opt., 2015, 8(1):91-98. (in Chinese)

刘小芳, 王胜男, 许健, 等.简易法制备高量子产率荧光材料及其应用[J].应用化学, 2018, 35(6):674-678.

LIU X F, WANG S N, XU J, et al.. Facile preparation and application of fluorescent material with high quantum yield[J].Chin. J. Appl. Chem., 2018, 35(6):674-678. (in Chinese)

HIDE F, DÍAZ-GARCÍAM A, SCHWARTZ B J, et al.. Semiconducting polymers:a new class of solid-state laser materials[J].Science, 1996, 273(5283):1833-1836.

SAMUEL I D W, TURNBULL G A. Organic semiconductor lasers[J].Chem. Rev., 2007, 107(4):1272-1295.

ZHANG C, ZOU C L, YAN Y L, et al.. Two-photon pumped lasing in single-crystal organic nanowireexcitonpolaritonresonators[J].J. Am. Chem. Soc., 2011, 133(19):7276-7279.

KWOK R T K, LEUNG C W T, LAM J W Y, et al.. Biosensing by luminogens with aggregation-induced emission characteristics[J].Chem. Soc. Rev., 2015, 44(13):4228-4238.

ZHU H, FAN J L, DU J J, et al.. Fluorescent probes for sensing and imaging within specific cellular organelles[J].Acc. Chem. Res., 2016, 49(10):2115-2126.

NIU G L, ZHANG R Y, KWONG J P C, et al.. Specific two-photon imaging of live cellular and deep-tissue lipid droplets by lipophilic AIE gens at ultralow concentration[J].Chem. Mater., 2018, 30(14):4778-4787.

SAGARA Y, YAMANE S, MITANI M, et al.. Mechanoresponsive luminescent molecular assemblies:an emerging class of materials[J].Adv. Mater., 2016, 28(6):1073-1095.

KUMAR K, DUAN H G, HEGDE R S, et al.. Printing colour at the optical diffraction limit[J].Nat. Nanotechnol., 2012, 7(9):557-561.

LU Y Q, ZHAO J B, ZHANG R, et al..Tunable lifetime multiplexing using luminescent nanocrystals[J].Nat. Photonics, 2014, 8(1):32-36.

WU H, CHEN Y, LIU Y. Reversibly photoswitchable supramolecular assembly and its application as a photoerasable fluorescent ink[J].Adv. Mater., 2017, 29(10):1605271-1-5.

BERAM K, PAL P, MALIK S. Solid-state emissive organic chromophores:design, strategy and building blocks[J].J. Mater. Chem. C, 2020, 8(3):788-802.

杨兵, 马於光, 沈家骢. π-共轭分子堆积、光电性能与超分子调控[J].高等学校化学学报, 2008, 29(12):2643-2658.

YANG B, MA Y G, SHEN J C. Stacking mode, optoelectronic property and supramolecular control method in π-conjugated organic molecules[J].Chem. J. Chin. Univ., 2008, 29(12):2643-2658. (in Chinese)

段炼, 邱勇.有机发光材料与器件研究进展[J].材料研究学报, 2015, 29(5):321-336.

DUAN L, QIU Y. Recent advances in organic electroluminescent materials and devices[J].Chin. J. Mater. Res., 2015, 29(5):321-336. (in Chinese)

SAGARA Y, KATO T. Mechanically induced luminescence changes in molecular assemblies[J].Nat. Chem., 2009, 1(8):605-610.

XIE Z Q, YANG B, CHENG G, et al.. Supramolecular interactions induced fluorescence in crystal:anomalous emission of 2, 5-diphenyl-1, 4-distyrylbenzene with all cis double bonds[J].Chem. Mater., 2005, 17(6):1287-1289.

HE F, XU H, YANG B, et al.. Oligomericphenylenevinylene with cross dipole arrangement and amorphous morphology:enhanced solid-state luminescence efficiency and electroluminescence performance[J].Adv. Mater., 2005, 17(22):2710-2714.

HONG Y N, LAM J W Y, TANG B Z. Aggregation-induced emission[J].Chem. Soc. Rev., 2011, 40(11):5361-5388.

MEI J, HONG Y N, LAM J W Y, et al.. Aggregation-induced emission:the whole is more brilliant than the parts[J].Adv. Mater., 2014, 26(31):5429-5479.

FENG H T, YUAN Y X, XIONG J B, et al.. Macrocycles and cages based on tetraphenylethylene with aggregation-induced emission effect[J].Chem. Soc. Rev., 2018, 47(19):7452-7476.

赵跃智, 蔡敏敏, 钱妍, 等.聚集诱导发光体系:化合物种类、发光机制及其应用[J].化学进展, 2013, 25(2-3):296-321.

ZHAO Y Z, CAI M M, QIAN Y, et al.. The systems with aggregation Induced emission:compounds, emission mechanisms and their applications[J]Prog. Chem., 2013, 25(2-3):296-321. (in Chinese)

ZHANG Z Y, LIU Y. Ultralong room-temperature phosphorescence of a solid-state supramolecule between phenylmethylpyridinium and cucurbit [6] uril[J].Chem. Sci., 2019, 10(33):7773-7778.

ZHANG Z Y, XU W W, XU W S, et al.. A synergistic enhancement strategy for realizing ultralong and efficient room-temperature phosphorescence[J].Angew. Chem. Int. Ed., 2020, 59(42):18748-18754.

JIN W H, LU H H, ZHANG Q, et al.. A dual-mode orthogonally tunable fluorescent system covering the whole white light region[J].Mater. Chem. Front., 2020, 4(2):532-536.

WANG Q, ZHANG Q, ZHANG Q W, et al.. Color-tunable single-fluorophore supramolecular system with assembly-encoded emission[J].Nat. Commun., 2020, 11(1):158.

CHRISTOFFERS J. Diaminoterephthalate fluorescence dyes-versatile tools for life sciences and materials science[J].Eur. J. Org. Chem., 2018, 2018(20-21):2366-2377.

SHIMIZU M, TAKEDA Y, HIGASHI M, et al.. 1, 4-Bis(alkenyl)-2, 5-dipiperidinobenzenes:minimal fluorophores exhibiting highly efficient emission in the solid state[J].Angew. Chem. Int. Ed., 2009, 48(20):3653-3656.

BEPPU T, TOMIGUCHI K, MASUHARA A, et al.. Single benzene green fluorophore:solid-state emissive, water-soluble, and solvent- and pH-independent fluorescence with large Stokes shifts[J].Angew. Chem. Int. Ed., 2015, 54(25):7332-7335.

TANG B L, WANG C G, WANG Y, et al.. Efficient red-emissive organic crystals with amplified spontaneous emissions based on a single benzene framework[J].Angew. Chem. Int. Ed., 2017, 56(41):12543-12547.

HUANG R, LIU B, WANG C G, et al.. Constructing full-color highly emissive organic solids based on an X-shaped tetrasubstituted benzene skeleton[J].J. Phys. Chem. C, 2018, 122(19):10510-10518.

TANG B L, ZHANG Z L, LIU H P, et al.. Amplified spontaneous emission, optical waveguide and polarized emission based on 2, 5-diaminoterephthalates[J].Chin. Chem. Lett., 2017, 28(11):2129-2132.

HUANG R, WANG C G, WANG Y, et al.. Elastic self-doping organic single crystals exhibiting flexible optical waveguide and amplified spontaneous emission[J].Adv. Mater., 2018, 30(21):1800814.

HUANG R, TANG B L, YE K Q, et al.. Flexible luminescent organic bulk crystal:2D elasticity toward 3D optical waveguide[J].Adv. Opt. Mater., 2019, 7(22):1900927.

PFLANTZ R, CHRISTOFFERS J. Diaminoterephthalates:scaffolds for combinatorial chemistry[J].J. Chem. Eur. J., 2009, 15(9):2200-2209.

LI S H, XU X F, ZHOU Y, et al.. Reversibly tunable white-light emissions of styrylpyridiniums with cucurbiturils in aqueous solution[J].Org. Lett., 2017, 19(24):6650-6653.

REN W, LIN G G, CLARKE C, et al.. Optical nanomaterials and enabling technologies for high-security-level anticounterfeiting[J].Adv. Mater., 2020, 32(18):1901430-1-15.

鞠乐, 张婷, 秦天游, 等.通过开关单元调节赋予荧烷水致变色性质及喷水打印应用[J].应用化学, 2019, 36(2):137-145.

JU L, ZHANG T, QIN T Y, et al.. Endowing hydrochromism to fluoranes by modifying their switch sites and their applications in water-jet printing[J].Chin. J. Appl. Chem., 2019, 36(2):137-145. (in Chinese)

李建华, 王洪泽, 盛兰, 等.无墨喷水可重复打印纸工业化制备[J].应用化学, 2018, 35(6):679-686.

LI J H, WANG H Z, SHENG L, et al.. Industrial preparation of water-jet rewritable paper[J].Chin. J. Appl. Chem., 2018, 35(6):679-686. (in Chinese)

BEATA J, JANINA K, JERZY P. Dichromophoric hemicyanine dyes. Synthesis and spectroscopic investigation[J].Dyes Pigm., 2007, 74(2):262-268.

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Hai-Xiang Mao

Bin-Bin Ding

Minjie Guo

Sheng-Hua Li

Biao Wang

Zhi Fan

Related Institution

College of Chemical Engineering and Materials Science， Tianjin University of Science & Technology

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