Creation of Novel Organic Fluorophores Containing Benzofuran Rings

含有苯并呋喃环的新型有机荧光团的创建

• 批准号: 16550131
• 负责人: YAMAGUCHI Yoshihiro
• 金额: $ 1.98万
• 依托单位: Kinki University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2004
• 资助国家: 日本
• 起止时间: 2004 至 2005
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-16550131/
• 关键词: Synthesis; Organic Fluorophores; Benzofuran; Phenyleneethynylene; Molecular Function; Light-emitting Characteristics; Organic Electroluminescence Material; πConjugation

Organic fluorophores are expected to play important roles in the extreme technology of 21st century as photoelectronics materials (e.g., organic electroluminescence diodes (OLEDs)). That is, these are expected to be not only the next generation of materials for the flat-panel display but also sources of light for illuminations, because the realization of white light-emitting may be possible on account of their flexibility of light-emitting color. In order to develop the further research in these fields, it is necessary to create the strongly fluorescent molecules at desired wavelength region. Under such circumstances, based on our previous results in regard to organic fluorophores, we have investigated on the creation of novel organic fluorophores and develop the general methodology. In conclusion, we have found out the following subjects.1.Phenyleneethynylenes containing pyridine rings : we have succeeded in creating very intense blue light-emitter, and found out that banana-shaped sy … More stems (having 2,6-disubstituted pyridine rings) show the greater light-emitting efficiency than the corresponding rod-shaped systems (2,5-disubstituted pyridine rings). Thus, we proposed the new concept that the higher emissive efficiency of banana-shaped systems might depend on the movability of the dipolar structural unit in the excited singlet state. This concept will be sure to make a contribution to creation of strongly fluorescent molecules.2.Linear-shaped systems introduced benzofuran rings to molecules : we have succeeded in the synthesis of very intense blue light-emitters having a single emissive maximum to suggest that the introduction of benzofuran rings to molecules is so effective for the creation of organic strongly fluorescent molecules.3.Rod-shaped oligo(aryleneethynylene)s (para-substituted systems) : we investigated the light-emitting efficiency tuning of rod-shaped oligo(p-phenylene ethynylen)s (OPEs, trimeric to pentameric systems) by donor- and acceptor-groups so that they emit the very intense fluorescence (Φ_f【approximately equal】1.0, log ε【approximately equal】5) at the desired wavelength region. This goal was achieved by side modification by MeO (donor) groups and end modification by CN-substituted benzene ring (or side modification by CN (acceptor) groups and end modification by NMe_2-substituted benzene ring) of tetrameric p-phenylene ethynylene rod-shaped molecule.4.Star-shaped oligo(aryleneethynylene)s (tiple mata-substituted systems) : we have investigated the light-emitting characteristics and occurrence of conjugation between arms of star-shaped rigid molecules that comprise a 1,3,5-tri-ethynylbenzene core, and methoxy group-substituted oligo(p-phenylethynylene)s arms. Consequently, we achieved the ultimate goal (Φ_f【approximately equal】1.0, log ε > 5) for organic molecules with respect to light-emitting ability by creating very intense violet-blue (Φ_f:0.97, log ε:5.11) and blue (Φ_f:0.98, log ε:5.29) bright light-emitters. Also π conjugation was found to occur between the arms of star-shaped rigid molecules despite the triple meta-substituted system. Less

有机荧光团有望在21世纪的极端技术中作为光电子材料（例如，有机电致发光二极管（OLED））。也就是说，这些材料不仅有望成为平板显示器的下一代材料，而且有望成为照明光源，因为由于它们的发光颜色的灵活性，白色发光的实现是可能的。为了在这些领域开展进一步的研究，有必要在所需的波长范围内产生强荧光分子。在这种情况下，基于我们以前的结果，在有机荧光团，我们已经研究了创造新的有机荧光团和发展的一般方法。总之，我们发现了以下几个问题：1.含吡啶环的苯乙炔：我们成功地创造了非常强的蓝光发射体，并发现香蕉形的系统， ...更多信息 茎（具有2，6-二取代的吡啶环）显示出比相应的棒状体系（2，5-二取代的吡啶环）更高的发光效率。因此，我们提出了香蕉形体系的高发射效率可能取决于激发单重态偶极结构单元的可动性的新概念。这一概念必将为强荧光分子的产生做出贡献。2.线性体系将苯并呋喃环引入分子中：我们已经成功地合成了具有单一发射最大值的非常强的蓝光发射体，这表明将苯并呋喃环引入到分子中对于产生有机强荧光分子是如此有效。（aryleneethynylene）s（对位取代体系）：我们研究了棒状寡聚（对苯乙炔）s（OPEs，三聚体到五聚体体系）的发光效率，通过给体和受体基团使它们在所需波长区域发射非常强的荧光（Φ_f[约等于]1.0，log ε[约等于]5）。这一目标是通过MeO（供体）基团的侧修饰和CN取代的苯环的末端修饰来实现的（或侧接CN（受体）基团，端接NMe_2取代苯环）。4.星形寡聚体亚芳基乙炔（三种替代系统）：我们已经研究了发光特性和包含1，3，5-三乙炔基苯核和甲氧基取代的低聚（对苯乙炔基）臂。因此，我们通过制备非常强的紫蓝色（Φ f：0.97，log ε：5.11）和蓝色（Φ f：0.98，log ε：5.29）发光体，实现了有机分子发光能力的最终目标（Φ f[约等于]1.0，log ε > 5）。此外，π共轭被发现发生在星形刚性分子的臂之间，尽管三重间位取代的系统。少

项目成果

New Fluorophores with Rod-Snaped Polycyano π-Conjugated Structures : Synthesis and Photophysical Properties.

具有棒状多氰基 π 共轭结构的新型荧光团：合成和光物理性质。

• 发表时间: 2006
• 期刊: Organic Letters 8・4
• 作者: Y.Yamaguchi;T.Ochi;T.Wakamiya;Y.Matsubara;Z.Yoshida
• 通讯作者: Z.Yoshida

Rigid Molecular Architectures That Comprise a 1,3,5-Tri-Substituted Characteristics and π Conjugation between The Arms.

包含 1,3,5-三取代特征和臂间 π 共轭的刚性分子结构。

• 发表时间: 2006
• 期刊: Journal of The American Chemical Society 128
• 作者: Y.Yamaguchi;T.Ochi;S.Miyamura;T.Tanaka;S.Kobayashi;T.Wakamiya;Y.Matsubara;Z.Yoshida
• 通讯作者: Z.Yoshida

Banana-Shaped Oligo(aryleneethynylene)s : Synthesis and Light-Emitting Characteristics.

香蕉形寡聚（亚芳基乙炔基）：合成和发光特性。

• 发表时间: 2005
• 期刊: Angewandte Chemie International Edition 44・43
• 作者: Y.Yamaguchi;S.Kobayashi;T.Wakamiya;Y.Matsubara;Z.Yoshida
• 通讯作者: Z.Yoshida

Rigid Molecular Architectures That Comprise a 1,3,5-Trisubstituted Benzene Core and Three Oligoaryleneethynylene Arms:Light-Emitting Characteristics and π Conjugation between the Arms

包含 1,3,5-三取代苯核和三个低聚亚芳基乙炔臂的刚性分子结构：发光特性和臂之间的 π 共轭

• 发表时间: 2006
• 期刊: J.Am.Chem.Soc. 128(14)
• 作者: Y. Imai;K. Kawaguchi;T. Harada;T. Sato;M. Ishikawa;M. Fujiki;R. Kuroda;Y. Matsubara;Y.Imai;T.Ochi;Y.Imai;Y.Yamaguchi;Y.Yamaguchi
• 通讯作者: Y.Yamaguchi

New Fluorophores with Rod-Shaped Polycyano π-Conjugated Structures : Synthesis and Photophysical Properties.

具有棒状多氰基 π 共轭结构的新型荧光团：合成和光物理性质。

• 发表时间: 2006
• 期刊: Org. Lett. 8(4)
• 作者: Y. Yamaguchi;T. Ochi;T. Wakamiya;Y. Matsubara;Z. Yoshida
• 通讯作者: Z. Yoshida