给受体型π-共轭有机分子的合成与性质研究
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摘要
近年来，含有给受体结构的π-共轭有机分子在染料敏化太阳能电池、有机发光二极管、双光子吸收、有机场效晶体管、传感器件等领域得到了广泛关注。三苯胺、吩噻嗪、咔唑均是富电子体系，具有很强的给电子能力和很好的空穴传输性能，由其衍生出的功能分子在光电领域显示出很好的竞争力。含有二米基硼的化合物在氟离子检测、有机发光二极管、双光子吸收和发射等方面有广泛的应用前景。本文合成了一系列新的含有三苯胺、吩噻嗪、咔唑、氰基丙烯酸、二米基硼等单元的给受体型π-共轭分子，研究了材料的光物理性质、电化学性质和荧光传感性质，取得如下创新性研究结果：
（1）利用Heck和Knoevenagel反应合成了分别以4-((E)-4-(二苯胺)苯乙烯基)-N-(4-((E)-4-(二苯胺)苯乙烯基)苯基)-N-苯基苯胺、4-((E)-2-(10-辛基-10H-吩噻嗪-3-基)乙烯基)-N-(4-((E)-2-(10-辛基-10H-吩噻嗪-3-基)乙烯基)苯基)-N-苯基苯胺、4-((E)-2-(9-辛基-9H-咔唑-3-基)乙烯基)-N-(4-((E)-2-(9-辛基-9H-咔唑-3-基)乙烯基)苯基)-N-苯基苯胺为给体、以氰基丙烯酸为受体的Y-形共轭分子TT、TP和TC，并将其作为染料敏化剂应用到染料敏化太阳能电池中，发现，Y-形π-共轭给体单元的引入不仅可以拓宽光谱的吸收范围，还能有效地抑制染料分子在二氧化钛表面的聚集，从而在一定程度上提高染料敏化太阳能电池器件的光伏性能。结果表明，以TT、TP和TC为染料敏化剂的太阳能电池的光电转化效率分别为5.12%，4.84%和3.63%，均高于以三苯胺为电子给体、氰基丙烯酸为受体的染料T敏化的染料敏化太阳能电池的光电转化效率(2.79%)。其中，基于TT的染料敏化太阳能电池的性能最好，短路电流为12.37mAcm-2、开路电压为0.72V。为拓宽染料在可见光区的吸收范围，我们增加了染料分子TT中的π-桥的共轭长度，将碳碳双键分别替换成呋喃乙烯基、噻吩乙烯基和苯乙烯基，得到了三种新的染料分子TT1，TT2和TT3。研究发现，在敏化剂中引入呋喃环、噻吩环可以有效地调节染料的HOMO和LUMO能级，拓宽光谱吸收范围，从而获得较大的IPCE值，提高器件的光电转化效率，其中，基于染料TT1(6.10%)和TT2(5.92%)的染料敏化太阳能电池器件的光电转化效率高于基于TT (5.12%)和TT3(4.97%)的器件。可见，提高染料分子的共轭程度可以拓宽其光谱吸收范围，提高开路电压，改善染料敏化太阳能电池器件的性能，本工作为应用于染料敏化太阳能的新型染料分子的设计提供了新思路。
（2）通过交替的Heck反应、Wittig反应以及亲核取代反应合成了三种受体为二米基硼，给体分别为吩噻嗪、三苯胺和三苯胺-吩噻嗪，桥连单元分别为芴乙烯基噻吩、芴乙烯基噻吩和乙烯基噻吩，具有D-π-A结构的二米基硼衍生物PFTB、TFTB和TPTB。研究发现，当加入氟离子后，上述三个化合物的溶液能快速地由黄色变为黄绿色，实现可视化的氟离子检测，同时，溶液的荧光显著增强。在其它阴离子Cl-, Br-, I-, OAc-, HSO--4, H2PO4的存在下，这三个化合物仍然可以快速高效地检测氟离子，表现出很强的抗干扰能力，它们对氟离子的检出限分别为7.52×10-8molL-1(PFTB)、7.51×10-8molL-1(TFTB)、1.58×10-7molL-1(TPTB)。同时发现，PFTB表现出良好的双光子吸收的性质，例如，用可见光和近红外光照射PFTB的甲苯溶液时，分子可以发射较强的绿色荧光，PFTB在甲苯溶液中于865nm处的最大双光子吸收截面为1801GM，当加入氟离子后，其双光子吸收截面减小，双光子诱导的荧光发射峰由578nm蓝移到520nm。可见，PFTB可作为检测氟离子的双光子荧光传感材料。
另外，利用Stille偶联反应和亲核取代反应合成了噻吩桥连的四苯乙烯-二米基硼衍生物TPETB。研究发现，该化合物具有明显的聚集诱导荧光增强特性，固态时能发射强的蓝绿色荧光，荧光量子产率为0.40。有趣的是该化合物也可以选择性识别氟离子并且可以实现可视化检测氟离子（淡黄色变为无色）同时伴随荧光的减弱，其检测限为：1.67×10-8molL-1。本工作为双光子荧光探针的设计提供了基础。
（3）利用收敛合成法，通过交替的Heck反应和Wittig反应合成了以二代树状三苯胺为外围重复单元、以喹喔啉或2,3-二甲基喹喔啉为核的结构对称的D-π-A-π-D型分子(TBT和TBMT)，研究了它们的光物理和电化学性质。结果表明，这两个化合物在甲苯中能发射较强的黄色荧光，用罗丹明6G为参比时，其荧光量子产率分别为0.52和0.66。在薄膜状态下，分子的荧光发射发生显著红移，能发射较强的红色荧光，有望在有机发光二极管中得到应用。
Donor-Acceptor π-conjugated organic molecules have been receivedconsiderable attention in many fields, especially in DSSCs, light-emitting diodes, twophoton absorption, organic field-effect transistors, sensor devices, and so on.Triphenylamine, phenothiazine, carbazole are electron-rich systems, which havestrong electron donating ability, good hole transport and electron transport properties.And their derivatives display good competitive power in the photovoltaic fields. Inaddition, dimesitylboron derivatives have wide applications in fluoride ion detection,OLED, two photon absorption and emission etc. So, herein, we mainly focus thesynthesis of a series of multifunctional donor-acceptor π-conjugated organicmolecules from triphenylamine, phenothiazine, carbazole, cyanoacrylic acid anddimesitylboron and the investigations of their photophysical, electrochemical andfluorescence sensing properties. And, some creative results have been obtained, whichwere outlined below:
(1) Three new Y-shaped cyanoacrylic acid derivatives TT、TPand TC have beensynthesized by Heck and Knoevenagel reactions in good yields, and their donor partswere4-((E)-4-(diphenylamino)styryl)-N-(4-((E)-4-(diphenylamino)styryl)phenyl)-N-phenylaniline,4-((E)-2-(10-octyl-10H-phenothiazin-3-yl)vinyl)-N-(4-((E)-2-(10-octyl-10H-phenothiazin-3-yl)vinyl)phenyl)-N-phenylaniline,4-((E)-2-(9-octyl-9H-carbazol-3-yl)vinyl)-N-(4-((E)-2-(9-octyl-9H-carbazol-3-yl)vinyl)phenyl)-N-phenylaniline, respectively, and the acceptor parts were all cyanoacrylic acid. The three newdyes have been used in dyes sensitized solar cells successfully. It was found that theintroduction of Y-shaped π-conjugated systems to the body not only can broaden thespectrum absorption range and can effectively inhibit the aggregation of dyemolecules in the surface of titanium dioxide due to their large spatial structure, and which greatly improved the photovoltaic performance of dye-sensitized solar celldevices. The total photo-to-electrical conversion efficiency (η) of DSSCs based onthese three new dyes (TT、TP and TC) were5.12%,4.84%and3.63%under AM1.5irradiation (100mW/cm2), which were all higher than that of dye T (2.79%)bearing only one triphenylamine as the donor. And the η of DSSC based on dye TTshowed the best photovoltaic performance and the Jscand Vocvalues in the TT-basedDSSC are12.37mA/cm2and0.72V. In order to extend the absorption range of dye inthe visible light region, we increase the π-bridge conjugation length of dye TT. Wesynthesized three new organic dye molecules TT1, TT2and TT3, whose π-units werevinyl furan, vinyl thiophene and vinylbenzene. It was found that the introduction offuran and thiophene π-linkers to the dyes could tune the HOMO-LUMO level,increase the spectral response range. So they could showed higher IPCE andincrease the total photo-to-electrical conversion efficiency. As a consequence, thesolar cells based on dye with furan and thiophene linker exhibit6.10and5.92%conversion efficiency, respectively, which were higher than that of TT3(4.97%) andTT (5.12%). So, increasing the conjugation degree of dye molecules can broaden thespectrum absorption range, improve the open circuit voltage, and improve the deviceperformance of dye-sensitized solar cells. So, this work will be helpful for us todesign new good dyes.
(2) Three new D-π-A dimesitylboron derivatives (PFTB、TFTB and TPTB)have been synthesized by Heck, Wittig and nucleophilic substitution reactions, wherethe acceptors were all dimesitylboron; the donor parts were phenothiazine,triphenylamine and triphenylamine-phenothiazine, respectively; and the bridge unitswere fluorene ethylene thiophene, fluorene ethylene thiophene and vinyl thiophene,respectively. It was found that the colors of these three compounds could change fromyellow to greenish yellow after being adding fluoride quickly, and it showed thesethree componds could selectively recognize fluoride anion by naked eyes. The threecompounds still could selectively recognize fluoride anion rapidly and efficiently inpresence of other anions Cl-, Br-, I-, OAc-, HSO-4, H2PO-4, which showed strong anti-interference ability. And it was found that the detection limits for F-were7.52×10-8molL-1（PFTB）、7.51×10-8molL-1（TFTB）and1.58×10-7molL-1（TPTB）.Moreover, it was found that they exhibited two photon absorption (TPA) ability, forexample, PFTB could emit strong green light under illumination by visible and nearIR light and the TPA cross sections of PFTB were1801GM at865nm in toluene.Upon addition of F-, the two-photon excited fluorescence emission band of PFTBblue-shifted from578nm to520nm upon adding F-, accompanied with the decreaseof TPA cross section. Therefore, PFTB can act as a TPA fluorescence probe fordetecting F-selectively.
A new TPE-dimesitylboron derivative (TPETB) based on TPE was synthesizedby Stille reaction and nucleophilic substitution reaction, where the bridge unit wasthiophene. It was found that it showed good AIE property and it could emitblueish-green fluorescence in the solid with high fluorescence quantum yield0.40. Itis interesting that TPETB could selectively recognize fluoride anion by naked eyes.Upon addition of F-, the color of the solution of TPETB in DCM turned into colorlessfrom pale yellow accompanied with the decrease of fluorescence intensity. And, it wasfound that the detection limit for F-was1.67×10-8mol/L. This work provided us anew strategy to design two photon fluorescence probes.
(3) Two π-conjugated D-π-A-π-D dendrimers (TBT and TBMT) bearing atriphenylamine moiety as dendrons, quinoxaline and2,3-dimethylquinoxaline as coreshave been synthesized through a convergent synthetic strategy, respectively. And theirphotophysical and electrochemical properties were also investigated. It was found thatthe two compounds could emit strong yellow light in toluene and their fluorescencequantum yields were0.52and0.66, respectively, according to rhodamine6G. Themaximum absorption and emission peaks in film were significantly red-shifted andcould emit strong red fluorescence in the film, which were good red emittingmaterials. The two compounds may be used in the OLED.
（1）利用Heck和Knoevenagel反应合成了分别以4-((E)-4-(二苯胺)苯乙烯基)-N-(4-((E)-4-(二苯胺)苯乙烯基)苯基)-N-苯基苯胺、4-((E)-2-(10-辛基-10H-吩噻嗪-3-基)乙烯基)-N-(4-((E)-2-(10-辛基-10H-吩噻嗪-3-基)乙烯基)苯基)-N-苯基苯胺、4-((E)-2-(9-辛基-9H-咔唑-3-基)乙烯基)-N-(4-((E)-2-(9-辛基-9H-咔唑-3-基)乙烯基)苯基)-N-苯基苯胺为给体、以氰基丙烯酸为受体的Y-形共轭分子TT、TP和TC，并将其作为染料敏化剂应用到染料敏化太阳能电池中，发现，Y-形π-共轭给体单元的引入不仅可以拓宽光谱的吸收范围，还能有效地抑制染料分子在二氧化钛表面的聚集，从而在一定程度上提高染料敏化太阳能电池器件的光伏性能。结果表明，以TT、TP和TC为染料敏化剂的太阳能电池的光电转化效率分别为5.12%，4.84%和3.63%，均高于以三苯胺为电子给体、氰基丙烯酸为受体的染料T敏化的染料敏化太阳能电池的光电转化效率(2.79%)。其中，基于TT的染料敏化太阳能电池的性能最好，短路电流为12.37mAcm-2、开路电压为0.72V。为拓宽染料在可见光区的吸收范围，我们增加了染料分子TT中的π-桥的共轭长度，将碳碳双键分别替换成呋喃乙烯基、噻吩乙烯基和苯乙烯基，得到了三种新的染料分子TT1，TT2和TT3。研究发现，在敏化剂中引入呋喃环、噻吩环可以有效地调节染料的HOMO和LUMO能级，拓宽光谱吸收范围，从而获得较大的IPCE值，提高器件的光电转化效率，其中，基于染料TT1(6.10%)和TT2(5.92%)的染料敏化太阳能电池器件的光电转化效率高于基于TT (5.12%)和TT3(4.97%)的器件。可见，提高染料分子的共轭程度可以拓宽其光谱吸收范围，提高开路电压，改善染料敏化太阳能电池器件的性能，本工作为应用于染料敏化太阳能的新型染料分子的设计提供了新思路。
（2）通过交替的Heck反应、Wittig反应以及亲核取代反应合成了三种受体为二米基硼，给体分别为吩噻嗪、三苯胺和三苯胺-吩噻嗪，桥连单元分别为芴乙烯基噻吩、芴乙烯基噻吩和乙烯基噻吩，具有D-π-A结构的二米基硼衍生物PFTB、TFTB和TPTB。研究发现，当加入氟离子后，上述三个化合物的溶液能快速地由黄色变为黄绿色，实现可视化的氟离子检测，同时，溶液的荧光显著增强。在其它阴离子Cl-, Br-, I-, OAc-, HSO--4, H2PO4的存在下，这三个化合物仍然可以快速高效地检测氟离子，表现出很强的抗干扰能力，它们对氟离子的检出限分别为7.52×10-8molL-1(PFTB)、7.51×10-8molL-1(TFTB)、1.58×10-7molL-1(TPTB)。同时发现，PFTB表现出良好的双光子吸收的性质，例如，用可见光和近红外光照射PFTB的甲苯溶液时，分子可以发射较强的绿色荧光，PFTB在甲苯溶液中于865nm处的最大双光子吸收截面为1801GM，当加入氟离子后，其双光子吸收截面减小，双光子诱导的荧光发射峰由578nm蓝移到520nm。可见，PFTB可作为检测氟离子的双光子荧光传感材料。
另外，利用Stille偶联反应和亲核取代反应合成了噻吩桥连的四苯乙烯-二米基硼衍生物TPETB。研究发现，该化合物具有明显的聚集诱导荧光增强特性，固态时能发射强的蓝绿色荧光，荧光量子产率为0.40。有趣的是该化合物也可以选择性识别氟离子并且可以实现可视化检测氟离子（淡黄色变为无色）同时伴随荧光的减弱，其检测限为：1.67×10-8molL-1。本工作为双光子荧光探针的设计提供了基础。
（3）利用收敛合成法，通过交替的Heck反应和Wittig反应合成了以二代树状三苯胺为外围重复单元、以喹喔啉或2,3-二甲基喹喔啉为核的结构对称的D-π-A-π-D型分子(TBT和TBMT)，研究了它们的光物理和电化学性质。结果表明，这两个化合物在甲苯中能发射较强的黄色荧光，用罗丹明6G为参比时，其荧光量子产率分别为0.52和0.66。在薄膜状态下，分子的荧光发射发生显著红移，能发射较强的红色荧光，有望在有机发光二极管中得到应用。
Donor-Acceptor π-conjugated organic molecules have been receivedconsiderable attention in many fields, especially in DSSCs, light-emitting diodes, twophoton absorption, organic field-effect transistors, sensor devices, and so on.Triphenylamine, phenothiazine, carbazole are electron-rich systems, which havestrong electron donating ability, good hole transport and electron transport properties.And their derivatives display good competitive power in the photovoltaic fields. Inaddition, dimesitylboron derivatives have wide applications in fluoride ion detection,OLED, two photon absorption and emission etc. So, herein, we mainly focus thesynthesis of a series of multifunctional donor-acceptor π-conjugated organicmolecules from triphenylamine, phenothiazine, carbazole, cyanoacrylic acid anddimesitylboron and the investigations of their photophysical, electrochemical andfluorescence sensing properties. And, some creative results have been obtained, whichwere outlined below:
(1) Three new Y-shaped cyanoacrylic acid derivatives TT、TPand TC have beensynthesized by Heck and Knoevenagel reactions in good yields, and their donor partswere4-((E)-4-(diphenylamino)styryl)-N-(4-((E)-4-(diphenylamino)styryl)phenyl)-N-phenylaniline,4-((E)-2-(10-octyl-10H-phenothiazin-3-yl)vinyl)-N-(4-((E)-2-(10-octyl-10H-phenothiazin-3-yl)vinyl)phenyl)-N-phenylaniline,4-((E)-2-(9-octyl-9H-carbazol-3-yl)vinyl)-N-(4-((E)-2-(9-octyl-9H-carbazol-3-yl)vinyl)phenyl)-N-phenylaniline, respectively, and the acceptor parts were all cyanoacrylic acid. The three newdyes have been used in dyes sensitized solar cells successfully. It was found that theintroduction of Y-shaped π-conjugated systems to the body not only can broaden thespectrum absorption range and can effectively inhibit the aggregation of dyemolecules in the surface of titanium dioxide due to their large spatial structure, and which greatly improved the photovoltaic performance of dye-sensitized solar celldevices. The total photo-to-electrical conversion efficiency (η) of DSSCs based onthese three new dyes (TT、TP and TC) were5.12%,4.84%and3.63%under AM1.5irradiation (100mW/cm2), which were all higher than that of dye T (2.79%)bearing only one triphenylamine as the donor. And the η of DSSC based on dye TTshowed the best photovoltaic performance and the Jscand Vocvalues in the TT-basedDSSC are12.37mA/cm2and0.72V. In order to extend the absorption range of dye inthe visible light region, we increase the π-bridge conjugation length of dye TT. Wesynthesized three new organic dye molecules TT1, TT2and TT3, whose π-units werevinyl furan, vinyl thiophene and vinylbenzene. It was found that the introduction offuran and thiophene π-linkers to the dyes could tune the HOMO-LUMO level,increase the spectral response range. So they could showed higher IPCE andincrease the total photo-to-electrical conversion efficiency. As a consequence, thesolar cells based on dye with furan and thiophene linker exhibit6.10and5.92%conversion efficiency, respectively, which were higher than that of TT3(4.97%) andTT (5.12%). So, increasing the conjugation degree of dye molecules can broaden thespectrum absorption range, improve the open circuit voltage, and improve the deviceperformance of dye-sensitized solar cells. So, this work will be helpful for us todesign new good dyes.
(2) Three new D-π-A dimesitylboron derivatives (PFTB、TFTB and TPTB)have been synthesized by Heck, Wittig and nucleophilic substitution reactions, wherethe acceptors were all dimesitylboron; the donor parts were phenothiazine,triphenylamine and triphenylamine-phenothiazine, respectively; and the bridge unitswere fluorene ethylene thiophene, fluorene ethylene thiophene and vinyl thiophene,respectively. It was found that the colors of these three compounds could change fromyellow to greenish yellow after being adding fluoride quickly, and it showed thesethree componds could selectively recognize fluoride anion by naked eyes. The threecompounds still could selectively recognize fluoride anion rapidly and efficiently inpresence of other anions Cl-, Br-, I-, OAc-, HSO-4, H2PO-4, which showed strong anti-interference ability. And it was found that the detection limits for F-were7.52×10-8molL-1（PFTB）、7.51×10-8molL-1（TFTB）and1.58×10-7molL-1（TPTB）.Moreover, it was found that they exhibited two photon absorption (TPA) ability, forexample, PFTB could emit strong green light under illumination by visible and nearIR light and the TPA cross sections of PFTB were1801GM at865nm in toluene.Upon addition of F-, the two-photon excited fluorescence emission band of PFTBblue-shifted from578nm to520nm upon adding F-, accompanied with the decreaseof TPA cross section. Therefore, PFTB can act as a TPA fluorescence probe fordetecting F-selectively.
A new TPE-dimesitylboron derivative (TPETB) based on TPE was synthesizedby Stille reaction and nucleophilic substitution reaction, where the bridge unit wasthiophene. It was found that it showed good AIE property and it could emitblueish-green fluorescence in the solid with high fluorescence quantum yield0.40. Itis interesting that TPETB could selectively recognize fluoride anion by naked eyes.Upon addition of F-, the color of the solution of TPETB in DCM turned into colorlessfrom pale yellow accompanied with the decrease of fluorescence intensity. And, it wasfound that the detection limit for F-was1.67×10-8mol/L. This work provided us anew strategy to design two photon fluorescence probes.
(3) Two π-conjugated D-π-A-π-D dendrimers (TBT and TBMT) bearing atriphenylamine moiety as dendrons, quinoxaline and2,3-dimethylquinoxaline as coreshave been synthesized through a convergent synthetic strategy, respectively. And theirphotophysical and electrochemical properties were also investigated. It was found thatthe two compounds could emit strong yellow light in toluene and their fluorescencequantum yields were0.52and0.66, respectively, according to rhodamine6G. Themaximum absorption and emission peaks in film were significantly red-shifted andcould emit strong red fluorescence in the film, which were good red emittingmaterials. The two compounds may be used in the OLED.
引文
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