271242-20-7Relevant articles and documents
Preparation of a cyclic polyphenylene array for a chiral-type carbon nanotube segment
Sekiguchi, Ryuta,Kudo, Shun,Kawakami, Jun,Sakai, Atsushi,Ikeda, Hiroshi,Nakamura, Hiromu,Ohta, Kazuchika,Ito, Shunji
, p. 1260 - 1275 (2016)
DielsAlder reaction of cyclic biphenylyleneacetylene compound 3 with tetraphenylcyclopentadienone (5) realized the preparation of large-sized cyclic polyphenylene array 4. This is the first example of a cyclic polyphenylene array with a complete ring arrangement of a chiral-type CNT segment with (12,3)-structure. Transformation of 4 to the chiral-type CNT segment was attempted, but resulted in the formation of a complicated mixture probably due to the partial dehydrogenation and/or the partial elimination about the long alkyl chains. Rather efficient blue emission of the cyclic compounds 3 and 4 was discussed utilizing fluorescence quantum efficiencies and lifetimes both in their solid state and in their solution. By thermal analyses triple-melting behavior of 3 was clarified.
Copolymers based on trialkylsilylethynyl-phenyl substituted benzodithiophene building blocks for efficient organic solar cells
Fan, Weili,Li, Huafeng,Liu, Haifen,Ning, Kaihua,Ren, Jingpeng,Su, Chao,Wang, Lixin,Zhu, Zixuan
, p. 19818 - 19825 (2021/11/12)
Non-fullerene acceptors have received a great deal of attention over the past several years, and numerous modifications on the molecular structures significantly boosted the power conversion efficiencies (PCEs) of organic solar cells (OSCs). To be a match, a promising polymer donor is urgently needed. Herein, we report a wide bandgap donor with alternating fluorinated benzotriazole (FTAZ) and triisopropylsilylethynyl-phenyl substituted benzodithiophene. Strategically, the lateral benzene and acetylene motifs induce a down-shift of the HOMO energy level, and the alkylsilyl facilitates inter-chain interactions and modulates the solubility. The new polymer exhibits a strong solution pre-aggregation ability that influences the intermixed morphology and optimizing methods of OSCs. When blended with the easily accessible acceptor IDIC, a respective PCE of 7.81% with aVocof 0.928 V has been demonstrated. We investigated the impact of molecular weights on the optical and electrochemical properties, charge transport, blend morphology, and photovoltaic parameters, and the result indicates that a highMnis desired for improving the quality of the solution-processed films. The acquired results reveal that trialkylsilylethynyl-phenyl is a promising multi-functional side chain scaffold for developing promising conjugated molecules.
Resistance to unwanted photo-oxidation of multi-acene molecules
Thomas, Samuel W. Iii,Yan, Yu,Lamport, Zachary A.,Kymissis, Ioannis
supporting information, p. 12731 - 12739 (2020/11/09)
Although long acenes remain a key class of π- conjugated molecules for numerous applications, photoinduced oxidation upon exposure of the acene to light, often through sensitization of 1O2, is an important reaction requiring mitigation for most applications. In response to this ongoing challenge, this paper presents a series of four new diarylethynyl-substituted long acenes-three tetracenes and one anthradithiophene-in which the arylene pendants are either benzene, naphthalene, or anthracene. UV/vis and fluorescence spectroscopy reveals that the anthracene-substituted derivatives fluoresce poorly (φ 0.01). Although all four long acenes react with 1O2 at expected rates when an external photosensitizer is included and show the expected changes in fluorescence to accompany these reactions, the anthracene-substituted derivatives resist direct photoinduced oxidation. Through a combination of mechanistic experiments, we conclude that rapid nonradiative decay of the anthracene-substituted derivatives, perhaps because of inter-arene torsions that emerge in theoretical geometry optimizations, makes these compounds poor photosensitizers for 1O2 or other reactive oxygen species. This discovery opens new design possibilities for extended acene structures with improved photochemical stability.
