Article
Chemistry, Organic
Yan-Ying Wu, Yi-Lin Wu, Cheng-Lan Lin, Hung-Cheng Chen, Yao-Yuan Chuang, Chih-Hsien Chen, Chih-Ming Chou
Summary: A strategy for the synthesis of dibenz-[a,j]-anthracenes (DBAs) from cyclohexa-2,5-diene-1-carboxylic acids is presented. The method involves sequential C-H olefination, cycloaddition, and decarboxylative aromatization, leading to regioselective ring formation and functional group introduction.
Article
Chemistry, Multidisciplinary
Weifan Wang, Fiona Hanindita, Yusei Tanaka, Kotaro Ochiai, Hiroyasu Sato, Yongxin Li, Takuma Yasuda, Shingo Ito
Summary: Sulfur-embedded polycyclic aromatic compounds have been widely used in the construction of organic semiconductors, but investigations on aromatic compounds containing thiepine, a sulfur-containing seven-membered-ring arene, have been limited. This study presents the synthesis and properties of pi-extended pyrrole-fused thiepine and oxepine compounds. A pi-extended pyrrole-fused thiepine exhibited a tilted pi-stacking structure in the crystal and demonstrated a high charge carrier mobility of up to 1.0 cm(2) V-1 s(-1) in single-crystal field-effect transistors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Masahito Murai, Shinji Iba, Sh ino Hamao, Yoshihiro Kubozono, Hiromi Ota, Kazuh iko Taka
Summary: By incorporating azulene into linearly pi-extended polycyclic aromatic hydrocarbons, we were able to reduce the HOMO-LUMO gap and maintain high stability under visible light. One of the derivatives exhibited typical p-type behavior under ambient conditions.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2023)
Article
Chemistry, Multidisciplinary
Yimin Liang, Shangshang Wang, Min Tang, Lin Wu, Lifang Bian, Liang Jiang, Zheng-Bin Tang, Jiali Liu, Aocong Guan, Zhichang Liu
Summary: In this study, we describe a one-pot synthesis of benzo[1,2-a:3,4-a':5,6-a'']triazulene (BTA) through a tandem reaction involving Suzuki coupling and Knoevenagel condensation. The resulting compound exhibits excellent stability, fluorescence, and large Stokes shifts. Additionally, its nitrated product, BTA-NO2, demonstrates unique solvatochromic effects and hydrogen-bonding-induced emission transfer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yushi Ohno, Shogo Ando, Daisuke Furusho, Ryoyu Hifumi, Yuuya Nagata, Ikuyoshi Tomita, Shinsuke Inagi
Summary: Here, a facile and selective synthesis of cationic azatriphenylene derivatives was achieved through electrochemical intramolecular cyclization, where the key step involves atom-economical C-H pyridination without a transition-metal catalyst or an oxidant. This proposed strategy provides a practical approach for introducing cationic nitrogen (N (+)) into pi-electron systems, thus expanding the molecular design of N (+)-doped polycyclic aromatic hydrocarbons.
Article
Chemistry, Applied
Changan Ji, Jie Yang, Siyi Hu, John Mack, Yongbo Zhang, Hua Lu, Lizhi Gai
Summary: The successful synthesis of stable seven-membered organoboron complexes enables the development of new functional dyes, which have been analyzed and compared to theoretical predictions. The presence of a seven-membered ring N,O boron-chelated moiety has been definitively confirmed, and one of the complexes has been shown to effectively permeate HeLa cells and selectively stain the cytoplasmic region. This synthetic strategy opens up new avenues for developing innovative materials.
Review
Chemistry, Organic
Khadimul Islam, Himani Narjinari, Akshai Kumar
Summary: Polyacetylene bridged PAHs are widely used in optoelectronic and sensing applications due to their tunable semiconductor and/or emissive behavior, low cost, and mechanical flexibility; The use of Sonogashira coupling in the synthesis of alkynyl bridged PAHs allows for the exploration of various photophysical properties and potential applications in novel pi-conjugated molecules.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Maria D. D. Matveeva, Tatyana Yu. Zheleznova, Anastasia S. S. Kostyuchenko, Almira R. R. Miftyakhova, Dmitry I. I. Zhilyaev, Leonid G. G. Voskressensky, Giovanni Talarico, Ilya V. V. Efimov
Summary: A series of novel BODIPYs with isoxazolyl groups at positions 1,7 were synthesized and their photophysical properties were characterized. The presence of isoxazolyl groups resulted in red-shifted long-wavelength absorption at 581 +/- 4 nm and emission at 622 +/- 3 nm in the near-infrared region. Three variants of substituents at positions 1,7 of BODIPY core were compared.
Article
Chemistry, Organic
Laiyun Zhou, Boming Wu, Yuanyuan Chen, Jianye Gong, Jianguo Wang, Gaole Dai, Chunyan Chi, Qing Wang
Summary: A nitrogenated derivative of Ovalene with all zigzag edges and nitrogen atom doping at the periphery has been successfully developed through one-step nitrogenation of formylbisanthene. These molecules exhibit decreased highest occupied molecular orbital levels, enhanced intermolecular interactions, and reversible acid response due to nitrogen incorporation. Additionally, the aza-ovalene also shows a diatropic ring current along the periphery, providing rare examples of all-zigzag-edged N-polycyclic aromatic hydrocarbons.
Article
Chemistry, Applied
Helio Lopes Barros, Maria Alexandra Esteves, Maria Joao Brites
Summary: In this work, the synthesis of two series of pyrene-pi-A compounds was reported. The incorporation of a fluorine atom on the pi-extension bridge caused a slightly red-shift at emission wavelength and an increase in the Stokes shift. Solvatochromic measurements and theoretical computational studies suggested a higher intramolecular charge transfer in the excited state for one series compared to the other due to stronger electron acceptor moieties. The synthesized pyrene derivatives exhibited good photophysical and thermal properties, making them potential candidates for OLED and LDS layers in stable perovskite solar cells.
Article
Chemistry, Organic
Kazumasa Funabiki, Kengo Yamada, Yuta Arisawa, Arina Watanabe, Tomohiro Agou, Yasuhiro Kubota, Toshiyasu Inuzuka, Yohei Miwa, Taro Udagawa, Shoichi Kutsumizu
Summary: A series of perfluoronaphthalene-based donor-acceptor-donor fluorescent dyes were successfully synthesized using a one-step route. The perfluoronaphthalene moiety served as a good electron-accepting aromatic ring with excellent intramolecular charge transfer properties. Replacing the naphthalene ring with perfluoronaphthalene stabilized the energy levels and reduced the energy band gap, leading to a change in the emission color. Among the synthesized dyes, those with diphenylamino groups showed the highest fluorescence quantum yields in solution and film, while the dye with carbazoyl group exhibited the highest fluorescence quantum yield in the crystalline state.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Khurnia Krisna Puji Pamungkas, Toshifumi Maruyama, Toshiaki Murai
Summary: A series of boron complexes were synthesized with a large Stokes shift, showing absorption and emission spectra almost independent of substituents and solvents. The nitrogen atom in the pyridyl group acted as a Lewis base, leading to a red-shift in absorption bands. Addition of certain acids resulted in a significant red-shift in absorption bands and fluorescence quenching.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Amira K. Hajri, Marzough A. Albalawi, Souad A. Moussa, Faouzi Aloui
Summary: In this study, three polycyclic aromatic hydrocarbons were synthesized and their optical properties were evaluated. The compounds exhibited unusual absorption and fluorescence characteristics, making them promising for optoelectronic applications.
LETTERS IN ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yumei Zhang, Xinnan Zhang, Qifan Yan
Summary: In this study, a series of conjugated organoborane oligomers with well-defined molecular structures and high brightness were prepared by coupling different building blocks. Optical measurements showed bathochromic shifts in absorption and emission maxima with increasing repeating units. Theoretical calculations were consistent with experimental results, and the method proved efficient for expanding small organoborane molecules into π-conjugated oligomers that emit different colors efficiently.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Anastasia S. Kostyuchenko, Evgenii B. Uliankin, Anton J. Stasyuk, Anna L. Samsonenko, Tatyana Yu Zheleznova, Anton L. Shatsauskas, Alexander S. Fisyuk
Summary: This article introduces a practical method for the preparation of benzo[1,2-d:4,3-d ']bis(thiazoles) using blue light-induced photochemical cyclization, and studies the photophysical and electrochemical properties of the synthesized compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)