CN110028427B - 含有9,10-双(二苯基亚甲基)蒽结构的压致荧光变色材料及其在压力检测中的应用 - Google Patents
含有9,10-双(二苯基亚甲基)蒽结构的压致荧光变色材料及其在压力检测中的应用 Download PDFInfo
- Publication number
- CN110028427B CN110028427B CN201910371019.XA CN201910371019A CN110028427B CN 110028427 B CN110028427 B CN 110028427B CN 201910371019 A CN201910371019 A CN 201910371019A CN 110028427 B CN110028427 B CN 110028427B
- Authority
- CN
- China
- Prior art keywords
- pressure
- bis
- diphenylmethylene
- fluorescence
- crystal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 26
- FOMBPKAPJZRPGJ-UHFFFAOYSA-N 9,10-dibenzhydrylideneanthracene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C2=CC=CC=1)C1=CC=CC=C1C2=C(C=1C=CC=CC=1)C1=CC=CC=C1 FOMBPKAPJZRPGJ-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000001514 detection method Methods 0.000 title claims abstract description 11
- 239000013078 crystal Substances 0.000 claims abstract description 17
- 230000035945 sensitivity Effects 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 230000008859 change Effects 0.000 abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 230000002093 peripheral effect Effects 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- -1 9, 10-bis (diphenylmethylene) anthracene compound Chemical class 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010979 ruby Substances 0.000 description 1
- 229910001750 ruby Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01L—MEASURING FORCE, STRESS, TORQUE, WORK, MECHANICAL POWER, MECHANICAL EFFICIENCY, OR FLUID PRESSURE
- G01L1/00—Measuring force or stress, in general
- G01L1/24—Measuring force or stress, in general by measuring variations of optical properties of material when it is stressed, e.g. by photoelastic stress analysis using infrared, visible light, ultraviolet
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
一种含有9,10‑双(二苯基亚甲基)蒽结构单元的压致荧光变色材料及其在压力检测中的应用，属于荧光材料技术领域。本发明在9,10‑双(二苯基亚甲基)蒽结构单元的***苯环的对位上引入四个氰基，使化合物晶体中形成松散而有序的排列方式，具有优异的高压下压致变色性能。其晶体的荧光发射峰位与外界压力的大小呈现线性关系，可通过荧光峰位的变化定量检测0‑14.7GPa范围内的外界压力，伴随荧光光谱上138nm的红移，检测的灵敏度为9.62nm GPa‑1，可实现对压力的定量检测。
Description
技术领域
本发明属于荧光材料技术领域，具体涉及一种含有9,10-双(二苯基亚甲基) 蒽结构单元的压致荧光变色材料，该压致变色荧光材料晶体的荧光发射峰位与外界压力的大小呈现线性关系，可通过荧光峰位的变化定量检测0～14.7GPa范围内的外界压力。
背景技术
有机压致荧光变色材料用途广泛，它不仅可以作为传感器、信息显示器和存储器等被应用于显示屏、安保***和记录器中，它还可应用于多种新兴的领域，比如保密信纸、安全墨水等等。随着科学的发展和社会的进步，人们对可承受较高压力的具有特殊用途的有机小分子压致荧光变色材料的需求进一步增加，它们可用大型飞机风洞实验，压力传感器等领域。因此开发出新型可在高压下表现出压致荧光变色功能的材料具有重要意义。
有机小分子荧光材料作为传感器具有灵敏度高、响应时间短、可视性等优点。如果用压致荧光变色材料作为压力荧光传感器，必须满足两个条件：一是明显的荧光颜色改变，二是高的灵敏度。目前虽然已有一些关于高压下具有压致荧光变色材料的报道，但是由于缺乏对此类分子构效关系的深入研究和高压下压致变色有机小分子设计理论的缺失，导致了此类分子的设计较为困难，而对于如何提高有机小分子在高压下的灵敏度更是未见报道。
具有确定分子量的高纯度9,10-双(二苯基亚甲基)蒽类化合物，是一种具有良好荧光性能的结构单元，对具有9,10-双(二苯基亚甲基)蒽结构的衍生物的聚集诱导发光性能和压致变色性能的研究非常多，但是对于具有9,10-双(二苯基亚甲基)蒽结构单元的分子的在高压条件下的压致荧光变色材料方面研究尚未见报道。近两年，有相关研究报道，如唐本忠教授课题组设计、制备了基于给体-受体原理的具有聚集诱导发光性能的在常压下具有压致荧光变色性质的材料 (Zikai He,Liuqing Zhang,Ju Mei,Tian Zhang,JackyW.Y.Lam,Zhigang Shuai, Yong Qiang Dong,Ben Zhong Tang,Chem.Mater.2015,27,6601-6607)。然而，这一类的压致荧光变色材料在高压下的性质研究非常稀少。能够实现定量检测外界压力的9,10-双(二苯基亚甲基)蒽类化合物材料更是未见报道。
发明内容
针对已有技术的不足，本发明的目的在于提供一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料，其具有良好的光学稳定性，可用于压力传感方面，具有良好的颜色对比度和灵敏性。
本发明所述的一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料，其结构式如下所示：
本发明通过将刚性9,10-双(二苯基亚甲基)蒽大分子平面与二氰基二苯基相连，***苯环的对位上引入四个氰基，引入较大的空间位阻效应，使分子间形成松散而有序的排列方式，所得的材料M1具有优异的高压下变色性能。其反应式如下所示：
与现有技术相比，本发明具有以下有益效果：
(1)本发明将具有优异荧光性能的9,10-双(二苯基亚甲基)蒽与二氰基二苯基结构单元应用到高压下具有压致荧光变色材料领域，设计、合成了目标化合物，对其进行荧光性能和高压下压致变色性能的表征，扩展了其潜在应用范围。
(2)化合物可承受14.7GPa的高压，荧光波长的变化与外界压力的大小呈现线性关系，可实现对压力的定量检测，且具有良好的灵敏度。
附图说明
图1是本发明实施例1中化合物M1晶体从常压到逐步加高压至14.7GPa 前后吸收光谱图。
图2是本发明实施例1中化合物M1晶体从常压到逐步加高压至14.7GPa 前后荧光光谱图。
图3是本发明实施例1中化合物M1晶体从常压到逐步加高压至14.7GPa 前后荧光颜色对照图。随着压力从0增加至14.7GPa,M1晶体的荧光下发光颜色也从未加压力时的灰白色逐渐变至红色，亮度也随之逐渐变暗,至14.7GPa 时几乎看不到发光亮度。
图4是本发明实施例1中化合物M1晶体检测压力的灵敏度图。
具体实施方式
下面结合实施例1，对本发明做进一步的详细说明。
实施例1：
M1其制备方法，包括以下步骤：
取9,10-二(二溴亚甲基)-9,10-二氢9,10-双(二苯基亚甲基)蒽(519.86mg,1mmol)，4-硼酸氰基苯(1.18g,8.0mmol)，无水碳酸钾(2.21g,16.0mmol)，精制甲苯12mL，无水乙醇6mL和去离子水8mL加入到100mL单颈圆底烧瓶中，加入催化剂四(三苯基膦)钯(92.40mg,0.08mmol)，在氮气环境下升温至110℃反应48h。反应结束后，用二氯甲烷萃取有机相并旋干得到粗产品，以石油醚和二氯甲烷的混合溶剂(二者体积比为4:1)作为展开剂用柱层析分离得到黄色化合物M1 413.4mg，产率为68％。M1的核磁氢谱数据为1H NMR(500MHz, DMSO):δ(ppm)7.87(d,J＝8.0Hz,8H),7.80(d,J＝8.0Hz,8H),6.91–6.89(m,4H),6.87–6.83(m,4H)。
M1晶体制备方法：
取4mg M1粉末完全溶解在4mL良溶剂并置于干净干燥的10mL试管里，并在溶液上方缓慢加入1mL不良溶剂，然后用一小团棉花紧紧堵住试管开口处，再将试管放入500mL干净广口瓶中，并在广口瓶中加入100mL不良溶剂，同时在广口瓶外侧包裹锡纸来避光。将广口瓶静置在室温环境下7天，可得到若干稳定的黄色方块状晶体。其中试管中良溶剂可选二氯甲烷、三氯甲烷、四氢呋喃等溶剂，试管中和广口瓶中的不良溶剂可选无水甲醇、无水乙醇等溶剂。
实施例2：高压传感性能展示
选取M1晶体的晶粒大小在0.2mm×0.4mm×0.2mm为最佳，放入金刚石对顶砧装置，以红宝石为压力探测器，硅油为传压介质进行高压实验。如附图1 所示，在高压吸收光谱中，随着压力逐渐增大，当压力达到14.9GPa时，吸收带边由初始状态下416nm红移到了762nm，吸收带隙从3.0eV变化到1.6eV。如附图2所示，在高压荧光光谱中，稍一加压到0.2GPa，晶体颜色会迅速发生变化，且荧光强度降低，当压力增大至14.7GPa，晶体颜色已经由灰白色变至红色(附图3)，同时荧光光谱红移到了655nm，颜色变化138nm。如附图4所示，以加压过程中M1晶体的发射光谱峰位为纵坐标，压力为横坐标作图，荧光峰位的变化相对于压力的变化呈现线性关系，利用公式
(λ为荧光峰位波长，P为压力)计算图4的斜率，其中Pn-1为初始外界压力值,可以是附图4 上的线性拟合线上任意一点所对应的横坐标上的压力值,Pn为变化后的外界压力值,可以是附图4上的线性拟合线上,在Pn-1所对应的点之后的任意一点的横坐标上的压力值,λn-1是外界压力为Pn-1时对应的荧光峰位,λn是外界压力为Pn时对应的荧光峰位,该拟合线的斜率即为高压检测过程中的压制变色灵敏度,通过上述公式计算数值为9.62nm GPa-1。
虽然本发明以上实施例公开如上，但其并非用以限定本发明的保护范围，任何熟悉该技术的技术人员，在不脱离本发明的构思和范围内所作的更改与润饰，均应属于本发明的保护范围。
Claims (3)
1.一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料在压力检测中的应用，该含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料的结构式如下所示，
2.如权利要求1所述的一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料在压力检测中的应用，其特征在于：压致荧光变色材料晶体的荧光发射峰位与外界压力的大小呈现线性关系，用于检测0-14.7GPa的外界压力。
3.如权利要求2所述的一种含有9,10-双(二苯基亚甲基)蒽结构单元的压致荧光变色材料在压力检测中的应用，其特征在于：灵敏度为9.62nm GPa-1。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910371019.XA CN110028427B (zh) | 2019-05-06 | 2019-05-06 | 含有9,10-双(二苯基亚甲基)蒽结构的压致荧光变色材料及其在压力检测中的应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910371019.XA CN110028427B (zh) | 2019-05-06 | 2019-05-06 | 含有9,10-双(二苯基亚甲基)蒽结构的压致荧光变色材料及其在压力检测中的应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110028427A CN110028427A (zh) | 2019-07-19 |
| CN110028427B true CN110028427B (zh) | 2021-08-20 |
Family
ID=67241246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910371019.XA Active CN110028427B (zh) | 2019-05-06 | 2019-05-06 | 含有9,10-双(二苯基亚甲基)蒽结构的压致荧光变色材料及其在压力检测中的应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110028427B (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022011508A1 (en) * | 2020-07-13 | 2022-01-20 | Jilin University | Systems and methods for pressure measurement |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4414414A (en) * | 1981-09-14 | 1983-11-08 | The United States Of America As Represented By The Secretary Of The Army | 4,4'-Dithiodianil |
| JP2001131434A (ja) * | 1999-11-08 | 2001-05-15 | Chemiprokasei Kaisha Ltd | 光変性可能な発光性有機色素およびそれを用いたマルチカラー有機ｅｌ素子 |
| AU2003277826A1 (en) * | 2002-06-21 | 2004-01-06 | Case Western Reserve University | Color tunable photoluminescent blends |
| CN102603567B (zh) * | 2012-01-18 | 2014-06-04 | 浙江工业大学 | 一种二苯乙烯腈衍生物及制备方法和应用 |
| CN103102286B (zh) * | 2012-12-08 | 2014-12-03 | 浙江工业大学 | 一种三苯胺衍生物及其制备方法和应用 |
| KR102169515B1 (ko) * | 2013-08-30 | 2020-10-26 | 엘지디스플레이 주식회사 | 퀴논 유도체 및 이를 포함하는 유기전계발광소자 |
| CN103641743A (zh) * | 2013-12-09 | 2014-03-19 | 浙江工业大学 | 一种三苯乙烯腈衍生物及其制备方法和应用 |
| CN107382774A (zh) * | 2017-06-23 | 2017-11-24 | 湖州师范学院 | 一种二苯乙烯衍生物ze构型异构体和合成及其应用 |
| CN108912012A (zh) * | 2018-07-26 | 2018-11-30 | 浙江工业大学 | 一种力致比例变色材料及其制备方法 |
| CN109020805B (zh) * | 2018-08-03 | 2020-11-03 | 北京师范大学 | 一种超高压条件下荧光变色共晶材料及其制备方法 |
-
2019
- 2019-05-06 CN CN201910371019.XA patent/CN110028427B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN110028427A (zh) | 2019-07-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Feng et al. | Unique piezochromic fluorescence behavior of organic crystal of carbazole-substituted CNDSB | |
| Gao et al. | Tetraphenylethene-based β-diketonate boron complex: efficient aggregation-induced emission and high contrast mechanofluorochromism | |
| Gao et al. | Effects of alkyl chain length on aggregation-induced emission, self-assembly and mechanofluorochromism of tetraphenylethene modified multifunctional β-diketonate boron complexes | |
| Xu et al. | Twisted donor–acceptor cruciform fluorophores exhibiting strong solid emission, efficient aggregation-induced emission and high contrast mechanofluorochromism | |
| Ma et al. | Pressure induced the largest emission wavelength change in a single crystal | |
| Xue et al. | A highly sensitive fluorescent sensor based on small molecules doped in electrospun nanofibers: detection of explosives as well as color modulation | |
| Zhang et al. | A new organic far-red mechanofluorochromic compound derived from cyano-substituted diarylethene | |
| CN101891642B (zh) | 一种荧光化合物及其在检测痕量硝基苯类物质中的应用 | |
| CN101899021A (zh) | 一类荧光化合物及其在检测痕量甲基***中的应用 | |
| CN109880084B (zh) | 含三苯胺结构及四苯乙烯单元的共轭聚合物及其制备方法和在电致变色中的应用 | |
| Gu et al. | Polymer-stretching photoluminescent regulation by doping a single fluorescent molecule | |
| CN110028427B (zh) | 含有9,10-双(二苯基亚甲基)蒽结构的压致荧光变色材料及其在压力检测中的应用 | |
| CN113956181B (zh) | 对氰基乙烯衍生物、对氰基乙烯衍生物晶体及制备方法和应用 | |
| CN114890914B (zh) | 一种高效率红光发射的有机晶体及其在低温荧光传感中的应用 | |
| Song et al. | Conjugated polymers based on poly (fluorenylene ethynylene) s: syntheses and sensing performance for nitroaromatics | |
| CN109761991B (zh) | 具有长寿命室温磷光现象的材料、制备方法及用途 | |
| Gao et al. | Piezochromic luminescence of cyano substituted E/Z isomeric derivatives: different responses to external stimuli | |
| Zhang et al. | A rapid-response fluorescent film probe to DNT based on novel AIE materials | |
| Zhang et al. | Dependence of mechanofluorochromic property at room temperature on alkyl chain structure for β-diketone boron complex and its polymer blend film | |
| CN107759504B (zh) | 一种固液态均具较强荧光的双相有机荧光材料及制备方法 | |
| Yu et al. | Synthesis, characterization and aggregation-induced emission of alternating copolymers containing cyclophanes and tetraphenylethenes | |
| Zhang et al. | The reversible mechanofluorochromic property of an asymmetric diketonate boron complex at room temperature | |
| Yang et al. | Tetraphenylethylene fused pyrrolo [3, 2-b] pyrrole derivatives with reversible mechanofluorochromic and aggregation-induced emission enhancement characteristics | |
| CN108587034B (zh) | 一种力致比率变色聚合物及其制备方法 | |
| Orofino et al. | Fluorene‐containing tetraphenylethylene molecules as lasing materials |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |