CN112321619A - 一类含有8-(双苯乙炔基)-酯基的氟硼吡咯化合物及其合成和应用 - Google Patents
一类含有8-(双苯乙炔基)-酯基的氟硼吡咯化合物及其合成和应用 Download PDFInfo
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- CN112321619A CN112321619A CN202011065765.5A CN202011065765A CN112321619A CN 112321619 A CN112321619 A CN 112321619A CN 202011065765 A CN202011065765 A CN 202011065765A CN 112321619 A CN112321619 A CN 112321619A
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- liquid crystal
- acetylenyl
- benzoate
- iodobenzoate
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- 230000015572 biosynthetic process Effects 0.000 title description 18
- 238000003786 synthesis reaction Methods 0.000 title description 18
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 99
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000011159 matrix material Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
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- 239000002904 solvent Substances 0.000 claims description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 10
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 10
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 8
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 6
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- 229940095102 methyl benzoate Drugs 0.000 claims description 5
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- OVTCUIZCVUGJHS-UHFFFAOYSA-N dipyrrin Chemical compound C=1C=CNC=1C=C1C=CC=N1 OVTCUIZCVUGJHS-UHFFFAOYSA-N 0.000 claims description 4
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- GHICCUXQJBDNRN-UHFFFAOYSA-N 4-iodobenzoic acid Chemical compound OC(=O)C1=CC=C(I)C=C1 GHICCUXQJBDNRN-UHFFFAOYSA-N 0.000 claims description 3
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- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
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- RUTMLOOMDBLALZ-UHFFFAOYSA-N heptyl 4-iodobenzoate Chemical compound CCCCCCCOC(=O)C1=CC=C(I)C=C1 RUTMLOOMDBLALZ-UHFFFAOYSA-N 0.000 claims 2
- GKRXJASBZIAMBE-UHFFFAOYSA-N hexyl 4-iodobenzoate Chemical compound CCCCCCOC(=O)C1=CC=C(I)C=C1 GKRXJASBZIAMBE-UHFFFAOYSA-N 0.000 claims 2
- IGMHERNBFXRMKQ-UHFFFAOYSA-N octyl 4-iodobenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(I)C=C1 IGMHERNBFXRMKQ-UHFFFAOYSA-N 0.000 claims 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- VOEYTTFPVLPCKU-UHFFFAOYSA-N propyl 4-iodobenzoate Chemical compound CCCOC(=O)C1=CC=C(I)C=C1 VOEYTTFPVLPCKU-UHFFFAOYSA-N 0.000 claims 2
- MVIVDSWUOGNODP-UHFFFAOYSA-N 2-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1I MVIVDSWUOGNODP-UHFFFAOYSA-N 0.000 claims 1
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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Abstract
本发明公开了一类含有8‑(双苯乙炔基)‑酯基的氟硼吡咯化合物及其制备方法和应用,其具有A结构。本发明以氟硼吡咯为母体,通过Sonogashira偶联反应在8号位引入双苯乙炔刚性结构和酯基烷基链柔性结构,设计合成了一系列8‑(双苯乙炔基)‑酯基氟硼吡咯类二向色性染料。本发明化合物在二氯甲烷中最大发射波长均集中在518nm左右,呈现绿色荧光,在液晶E7中表现出良好的二向色比及有序参数;本发明的液晶化合物在50‑100℃范围内存在液晶中间相,可用于制造液晶显示产品,尤其是作为宾体染料用于宾主模式液晶显示器;本发明化合物添加至E7液晶并用于宾主显示模式时可提高响应时间,达到快速响应的效果。
Description
技术领域
本发明涉及8-(双苯乙炔基)-酯基的氟硼吡咯荧光液晶染料的制备方法和应用,属于显示材料领域。
背景技术
伴随着全球信息化、数字化的进程,电子信息产业正迎来平板化浪潮,一场显示领域的革命正在发生。风靡一时的阴极射线管显示器正逐渐被以薄膜晶体管液晶显示器件为代表的平板显示器所取代,平板显示技术和产品已居于显示领域的主导地位。理想的显示器应该具备以下特点:低工作电压、低能耗、体积小、质量轻、对比度高、响应速度快、广视角等。宾-主”液晶显示是近代科学发展的新领域之一。
“宾-主”型液晶显示器之所以能成为一类有应用前景的显示器,正是因为其不仅显示信息色彩鲜艳、亮度高、对比度好、视角宽,而且在组装时只需要使用一片偏光片甚至不使用偏光片,这就大大提高了背光源的光利用率。尤其近年来荧光二向色性液晶化合物的发展,将其应用于“宾-主”显示中,能将发射型显示器的鲜艳色光和高亮度与液晶显示器的特点结合起来,可以成为一种能耗更低的便携电子产品显示器。目前所研究的二向性液晶化合物的结构和品种少,设计合成研究性能优异且满足实际应用条件的新型二向色性液晶化合物具有重要意义。
发明内容
为解决现有技术中存在的缺少性能良好的荧光二向色性液晶化合物的问题,本发明提供一种呈现绿色荧光、具有高荧光量子产率、在液晶E7中表现出较好的二向色比以及有序参数、适用于液晶显示产品的荧光二向色性液晶化合物。
本发明的技术目的之一在于提供一类新型的荧光二向性液晶化合物。
8-(双苯乙炔基)-酯基氟硼吡咯类荧光二向色性液晶化合物,所述液晶化合物具有以下的化学分子结构通式A:
R选自甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基和正辛基中的一种。
本发明的另一技术目的在于提供上述荧光二向色性液晶化合物的制备方法,包括以下步骤:
以2.4-二甲基吡咯和乙酰氯为原料,以二氯甲烷做溶剂与三氟化硼乙醚络合物配位生成氟化硼络合二吡咯甲川类母体,氟化硼络合二吡咯甲川类母体与4-乙炔基苯甲酸甲酯、4-乙炔基苯甲酸己酯通过Sonogashira偶联反应后连接,得到所述液晶化合物。
所述4-乙炔基苯甲酸甲酯、4-乙炔基苯甲酸己酯选自4-乙炔基苯甲酸甲酯、4-乙炔基苯甲酸乙酯、4-乙炔基苯甲酸丙酯、4-乙炔基苯甲酸丁酯、4-乙炔基苯甲酸戊酯、4-乙炔基苯甲酸己酯、4-乙炔基苯甲酸庚酯、4-乙炔基苯甲酸辛酯。
具体合成路线如下:
将对碘苯甲酸和甲醇二者按摩尔比1:3进行反应,同时加入二环己基碳二亚胺(DCC)和4-二甲氨基吡啶(DMAP),常温反应至反应完全,过滤,用硅胶柱层析法进行分离提纯得化合物1。
进一步地,化合物1溶解在无水三乙胺溶剂中,加入催化剂量的碘化亚铜、三苯基膦和二三苯基膦二氯化钯作为催化剂。再加入等量三甲基硅乙炔,80℃下氮气保护回流反应8h,TLC检测反应完全,过硅胶层析柱得化合物2。
进一步地,化合2溶解在无水二氯甲烷溶剂中,加入3倍量碳酸钾,室温反应2h,TLC检测反应完全,过硅胶层析柱得化合物3。
进一步地,将对碘苯甲酰氯和2,4-二甲基吡咯按摩尔比1:2在常温下反应,加入催化量的三乙胺,过半小时加入适量的三氟化硼乙醚,TLC跟踪监测至反应完全减压除去多余溶剂,红褐色固体粗产物过硅胶柱层析,得化合物4。
进一步地,化合物4与化合物3以1:1摩尔比进行混合,同时加入催化量的二三苯基膦二氯化钯、三苯基膦、CuI等催化剂,用干燥三乙胺作为缚酸剂和溶剂。回流反应8-10小时,过硅胶柱分离,得固体化合物A即为所述液晶染料。
进一步地,在上述技术方案中,R选自甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基和正辛基中的一种。
本发明提供上述的化合物作为荧光二向色性液晶化合物的应用。
本发明提供的上述液晶化合物具有液晶相,作为液晶化合物的应用。
本发明另一方面提供上述荧光二向色性液晶化合物在制造液晶显示产品中的应用。所述的液晶显示产品是宾主型液晶显示器。具体地,是用作宾体液晶化合物,应用于制备宾主型液晶显示器。
本发明再一方面的目的在于提供一类宾主型液晶显示器,所述的液晶显示器以本发明所述的荧光二向性液晶化合物作为宾体液晶液晶化合物。
本发明提供上述化合物作为液晶材料的应用,所述液晶材料为彩色液晶材料。本发明的有益效果:
第一、以氟硼吡咯为母体,合成同时含有双苯乙炔的刚性结构和酯基官能团柔性结构的液晶染料,结构新颖,丰富了荧光二向性染料的种类;
第二、通过修饰BODIPY的8号位,保留了氟硼吡咯类荧光染料优异的光化学物理性能,如较高的摩尔消光系数、单色性良好的荧光和较高的光稳定性等;
第三、在含(双苯乙炔基)-酯基柔性结构中引入含氟的BODIPY结构,有利于降低化合物的粘度、提高二向色比、有序参数和介电各向异性等;
第四、将本发明中的化合物作为宾体染料加入主体液晶E7,其中的酯基柔性结构有利于降低主体液晶的响应时间,最低降低了4.58ms;
本发明的荧光二向性染料在液晶中具有较高的二向色比以及有序参数,其中二向色比最大为7.37,有序参数最大为0.68,可用于制造宾主液晶显示器,作为宾体液晶染料。
附图说明
图1为制备的液晶化合物A2的差示扫描量热图;
图2为液晶化合物A1在主体液晶E7中响应时间图;
图3为液晶化合物A2在主体液晶E7中响应时间图。
具体实施方式
下述非限制性实施例可以使本领域的普通技术人员更全面地理解本发明,但不以任何方式限制本发明。
实施例1
荧光二向色性液晶化合物A1的合成
中间体(1)的合成
50ml两口瓶中加入1.02g对碘苯甲酸,0.4ml甲醇,溶于20mL二氯甲烷中,再向反应体系中加入3g二环己基碳二亚胺(DCC)和600mg4-二甲氨基吡啶DMAP,常温反应2h,用硅胶柱层析法进行分离提纯,洗脱液为石油醚:乙酸乙酯=40:1(V/V)。得白色固体2.28g,熔点113-115℃。
中间体(2)的合成
在50mL的圆底双口瓶中加入1.83g对碘苯甲酸甲酯,再加入12mL乙胺,加入40mg碘化亚铜、75mg三苯基膦和35mg二三苯基膦二氯化钯,加入0.05ml三甲基硅乙炔,反应2h。用乙酸乙酯萃取,减压除去溶剂得1.25g白色固体。
中间体(3)的合成
在50mL的双口瓶中加入1.25g中间体2,再加入1.2g碳酸钾(12mmol)0ml无水乙醇,常温反应1h,粗产物过硅胶柱层析,得固体720mg,产率75%。
中间体(4)的合成
将2.65g对碘苯甲酰氯和3ml的2,4-二甲基吡咯在常温下反应6小时后,加入4ml的三乙胺,5ml的三氟化硼乙醚,得固体粗产物过硅胶柱层析,减压除去溶剂得红色固体3.6g,产率80%。
目标产物(A1)的合成
在50mL的圆底双口瓶中加入128mg中间体3和336mg中间体4,再加10mL三乙胺,加入5mg碘化亚铜、10mg三苯基膦,回流反应8h。粗产物过硅胶层析柱,得270mg固体,产率70%。
1H NMR(400MHz,CDCl3)δ8.07(d,J=8.5Hz,2H),7.70(d,J=8.3Hz,2H),7.63(d,J=8.5Hz,2H),7.33(d,J=8.3Hz,2H),6.01(s,2H),4.14(q,J=7.1Hz,2H),3.96(s,3H),2.58(s,6H),2.06(s,3H),1.45(s,6H),1.28(t,J=7.1Hz,3H).
熔点:58-60℃,TOF MS EI+(m/z):C29H25BF2N2O2计算值:482.1977,实测值:482.1968
实施例2
荧光二向色性液晶化合物A2的合成
中间体(5)的合成
除用1.07ml正己醇代替甲醇外,其他操作步骤同实例1中中间体1的合成,得中间体5,无色液体3.05g,产率92%。
中间体(6)的合成
除用3.05中间体5代替中间体1外,其他操作步骤同实例1中中间体2的合成,得中间体6,白色固体2.3g,产率79%。
中间体(7)的合成
除用2.3g中间体6代替中间体2外,其他操作步骤同实例1中中间体3的合成,得中间体7,白色固体1.4g,产率79%。
目标产物(A2)的合成
除用184mg中间体7代替中间体3外,其他操作步骤同实例1中目标产物A1的合成,得目标产物A2,橘红色固体300mg,产率68%。
1H NMR(400MHz,CDCl3)δ8.07(d,J=8.3Hz,2H),7.70(d,J=8.0Hz,2H),7.63(d,J=8.2Hz,2H),7.33(d,J=8.0Hz,2H),6.01(s,2H),4.42(q,J=7.1Hz,2H),3.30–1.77(m,9H),1.58(s,3H),1.52–1.36(m,8H),1.28(t,J=7.1Hz,3H).
熔点:60℃,清亮点:99℃。TOF LD+(m/z):C34H35BF2N2O2,计算值:552.2760,实测值:552.2775
TOF LD+(m/z):C34H35BF2N2O2,计算值:552.2760,实测值:552.2775
本发明的荧光二向色性液晶化合物的性质测定:
(1)液晶化合物在二氯甲烷中的光谱性质测试:
液晶化合物测试浓度:液晶化合物在不同溶剂中的浓度为1.0×10-5mol/L。
液晶化合物荧光量子产率ΦF值的测定:以罗丹明B溶液为基准。代入式(1)计算:
式中:Φ(sample))、Φ(standard)别表示待测样品和标准物的荧光量子产率;Abs(standard)、Abs(sample)分别表示标准物和待测样品在激发波长下的吸收值;Flu(sample)、Flu(standard)分别表示待测样品和标准物的荧光强度。
对化合物A1,A2的测试结果如下:
表1.液晶化合物A1,A2在二氯甲烷中的紫外和荧光数据
液晶化合物A吸收波长在503nm,最大发射波长分别为518、517nm,呈现绿色荧光;能实现纯色显示;荧光量子产率分别为0.49,0.33。
(2)液晶化合物在液晶中的偏振光谱性质测试:
主体液晶为E7,将液晶化合物A按照浓度为0.5%的比例掺入到液晶中并装盒。分别测试液晶化合物与液晶盒取向膜平行方向上的吸光度A//和垂直方向上的吸光度A⊥、平行方向上的荧光强度F//和垂直方向上的荧光强度F⊥;并按照下列公式(2)、(3)、(4)、(5)计算出液晶化合物在液晶中的吸收有序参数SA、吸收二向色比DA和荧光有序参数SF、荧光二向色比DF:
化合物A1,A2偏振光谱测试结果如下:
表2.液晶化合物A在液晶E7中的偏振紫外和偏振荧光数据:
A1,A2在液晶E7中表现出较好的二向色比以及有序参数。A1吸收有序参数为0.57,吸收二向色比为4.94,荧光有序参数为0.57,荧光二向色比为4.91。A2吸收有序参数为0.68,吸收二向色比为7.37,荧光有序参数为0.69,荧光二向色比为7.57。
(3)二向性液晶化合物A的液晶行为
对制备的液晶化合物A系列化合物进行差热扫描,得到其差热扫描量热图(图1)。化合物A2在升温过程中的50℃-100℃呈现液晶相。
(4)液晶化合物A系列对主体液晶E7的影响
液晶响应时间的测量:主体液晶为E7;测试用液晶盒上下两基板的取向相互平行,盒厚度为20μm;将液晶化合物A按照浓度为0.5%的比例掺入到主体液晶E7中,在室温下混合均匀,封住灌晶口。分别测试宾体化合物A对主体液晶E7的影响。
用波长为510nm的绿光作为光源,通过检测器收集光源的透过情况。测试时样品的驱动电压为0-10V,相对亮度从10%到90%的时间为上升时间tr,从90%到10%为下降时间tf,响应时间为tr与tf之和,即tr+tf=t。
表3.宾体化合物A系列化合物在主体液晶E7中的响应时间数据
荧光二向色性液晶化合物A能够改变液晶的响应时间,可以缩短主体液晶E7的响应时间,响应时间最快为A2掺杂的主体液晶E7,最快可缩短约4.58ms。
Claims (9)
2.权利要求1所述化合物的制备方法,其特征在于包括以下步骤:
将对碘苯甲酰氯和2,4-二甲基吡咯作为原料,以二氯甲烷为溶剂并加入三乙胺,反应一段时间后再加入三氟化硼乙醚进行配位,合成氟化硼络合二吡咯甲川类母体,所述氟化硼络合二吡咯甲川类母体分别与4-乙炔基苯甲酸甲酯、4-乙炔基苯甲酸乙酯、4-乙炔基苯甲酸丙酯、4-乙炔基苯甲酸丁酯、4-乙炔基苯甲酸戊酯、4-乙炔基苯甲酸己酯、4-乙炔基苯甲酸庚酯、4-乙炔基苯甲酸辛酯通过Sonogashira偶联反应后连接,得到所述液晶染料化合物;
所述4-乙炔基苯甲酸甲酯、4-乙炔基苯甲酸乙酯、4-乙炔基苯甲酸丙酯、4-乙炔基苯甲酸丁酯、4-乙炔基苯甲酸戊酯、4-乙炔基苯甲酸己酯、4-乙炔基苯甲酸庚酯、4-乙炔基苯甲酸辛酯的制法为:以对碘苯甲酸为原料合成的对碘苯甲酸甲酯、对碘苯甲酸乙酯、对碘苯甲酸丙酯、对碘苯甲酸丁酯、对碘苯甲酸戊酯、对碘苯甲酸己酯、对碘苯甲酸庚酯、对碘苯甲酸辛酯,通过Sonogashira偶联反应与三甲基硅乙炔连接,再以甲醇为溶剂并加入3倍当量的碳酸钾,进行脱硅反应得到;
所述对碘苯甲酸甲酯、对碘苯甲酸乙酯、对碘苯甲酸丙酯、对碘苯甲酸丁酯、对碘苯甲酸戊酯、对碘苯甲酸己酯、对碘苯甲酸庚酯、对碘苯甲酸辛酯的制备方法分别为:对碘苯甲酸分别与甲醇、乙醇、正丙醇、正丁醇、正戊醇、正己醇、正庚醇、正辛醇以二氯甲烷为溶剂,加入1.5倍当量的二环己基碳二亚胺和催化量的4-二甲氨基吡啶,进行酯化反应得到。
3.权利要求1所述的化合物作为荧光二向色性染料的应用。
4.根据权利要求3所述的应用,其特征在于,所述染料为具有液晶相的染料。
5.根据权利要求1所述的化合物作为液晶材料的应用。
6.根据权利要求5所述应用,其特征在于,所述液晶材料为彩色液晶材料。
7.权利要求1所述的化合物作为荧光二向性液晶染料在制造液晶显示产品中的应用。
8.根据权利要求7所述的应用,其特征在于所述的液晶显示产品为宾主型液晶显示器。
9.一类宾主型液晶显示器,其特征在于:以权利要求1所述的化合物作为荧光二向性宾体液晶染料。
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