Synthesis and optical properties of pyrrolo[3,2-b]pyrrole-2,5(1 H,4 H)-dione (iDPP)-based molecules

Kirkus M.; Knippenberg S.; Beljonne D.; Cornil J.; Janssen R.A.J.; Meskers S.C.J.

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Synthesis and optical properties of pyrrolo[3,2-b]pyrrole-2,5(1 H,4 H)-dione (iDPP)-based molecules

机译：吡咯并[3,2-b]吡咯-2,5（1 H，4 H）-二酮（iDPP）基分子的合成和光学性质

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We describe the synthesis and photophysical properties of a series of derivatives of pyrrolo[3,2-b]pyrrole-2,5(1H,4H)-dione-3,6-diyl (iDPP) linked to two oligothiophenes of variable length (nT). The iso-DPP-oligothiophenes (iDPPnTs) differ from the common pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione-3,6-diyl-oligothiophene analogues (DPPnTs) by a different orientation of the two lactam rings in the bicyclic iDPP unit compared to DPP. In contrast to the highly fluorescent DPPnTs, the new isomeric iDPPnTs exhibit only very weak fluorescence. We demonstrate with the help of quantum-chemical calculations that this can be attributed to a different symmetry of the lowest excited state in iDPPnT (A in C_2 symmetry) compared to DPPnTs (B) and the corresponding loss in oscillator strength of the lowest energy transition. Upon extending the oligothiophene moiety in the iDPPnTs molecules, the charge transfer character of the lowest A excited state becomes more pronounced. This tends to preclude high fluorescence quantum yields even in extended iDPPnTs systems.

机译：我们描述了吡咯并[3,2-b]吡咯-2,5（5H（1H，4H）-dione-3,6-diyl（iDPP）与两个可变长度的寡聚噻吩连接的一系列衍生物的合成和光物理性质（ nT）。 iso-DPP-低聚噻吩（iDPPnTs）与常见的吡咯并[3,4-c]吡咯-1,4（2H，5H）-dione-3,6-diyl-低聚噻吩类似物（DPPnTs）不同与DPP相比，双环iDPP单元中的两个内酰胺环。与高荧光DPPnT相比，新的异构iDPPnT仅显示非常弱的荧光。我们借助量子化学计算证明，这可以归因于与DPPnTs（B）相比，iDPPnT的最低激发态的对称性（C_2对称性中的A）和最低能量跃迁的相应的振荡器强度损失。在iDPPnTs分子中延伸低聚噻吩部分后，最低A激发态的电荷转移特性变得更加明显。即使在扩展的iDPPnTs系统中，这也倾向于排除高荧光量子产率。

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《The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory》 |2013年第13期|共8页
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Kirkus M.; Knippenberg S.; Beljonne D.; Cornil J.; Janssen R.A.J.; Meskers S.C.J.;
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1. Synthesis and optical properties of pyrrolo[3,2-b]pyrrole-2,5(1 H,4 H)-dione (iDPP)-based molecules [J] . Kirkus M., Knippenberg S., Beljonne D., The journal of physical chemistry, A. Molecules, spectroscopy, kinetics, environment, & general theory . 2013,第13期

机译：吡咯并[3,2-b]吡咯-2,5（1 H，4 H）-二酮（iDPP）基分子的合成和光学性质
2. Synthesis of unsymmetrical pyrrolo[3,2-b]pyrrole-2,5-diones and bis(quinazolin-4-on-2-yls) by double-anion-capture reactions of unsymmetrical oxaldi(arylimidoyl) dichlorides [J] . Helmholz F, Schroeder R, Langer P Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2006,第15期

机译：不对称草酰二芳基酰二氯的双阴离子捕获反应合成不对称吡咯并[3,2-b]吡咯-2,5-二酮和双（喹唑啉-4-on-2-yls）
3. Synthesis of unsymmetrical pyrrolo[3,2-b]pyrrole-2,5-diones [J] . Langer P., Helmholz F., Schroeder R. Synlett . 2003,第15期

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4. Synthesis, Photochromic Properties and Application in Optical Memory of a Diarylethene Based on Pyrrole Ring [C] . Renjie Wang, Gang Liu, Shiqiang Cui, International Conference on Chemical, Material and Metallurgical Engineering . 2012

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8. Final Results of a Reproductive/Developmental Toxicity Screening Study in Rats with Orally Administered 3,6-Bis(4-tert-butylphenyl)-2,5-dihydropyrrolo(3,4-c)pyrrole-1,4-dione. [R] . 2014

机译：用口服给药的3,6-双（4-叔丁基苯基）-2,5-二氢吡咯并（3,4-c）吡咯-1,4-二酮对大鼠进行生殖/发育毒性筛选研究的最终结果。

Synthesis and optical properties of pyrrolo[3,2-b]pyrrole-2,5(1 H,4 H)-dione (iDPP)-based molecules

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