Article
Chemistry, Multidisciplinary
Sairam Dnyaneshwar Veer, Vivek Chandrakant Wakchaure, Kiran Asokan, Ruchi Dixit, Tanmay Goswami, Ramchandra Saha, Rajesh Gonnade, Hirendra N. Ghosh, Sukumaran Santhosh Babu
Summary: Aesthetic designs from nature inspire scientific models and enable new knowledge. The advantageous positioning of structural units in multicomponent macrocycles allows for efficient communication. However, the construction of a functionalizable macrocycle for ultrafast charge separation and stabilization has not been attempted. In this study, a new functionalizable macrocycle was synthesized and its charge separation and stabilization capabilities were observed. The design of our macrocycle, with a supportive spatial arrangement of donor and acceptor units, will inspire the development of more complex synthetic systems with exciting electron-transfer and charge-separation features.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Ying Wang, Qi Zhang, Junbo Gong, Xin Zhang
Summary: By twisting the aromatic -system structures, highly fluorescent dyes with fluorescence quantum yields close to 100% can be synthesized. These twisted dyes are more sensitive to microenvironment changes, suitable for optoelectrical devices and materials, and retain excellent optical properties.
Article
Chemistry, Organic
Xinyue Tian, Yao Xiao, Shuoyingjie Wang, Guanghua Liu, Wenhao Zhang, Laiyun Zhou, Jianye Gong, Xuejin Zhang, Xiang Li, He Meng, Jianguo Wang, Gaole Dai, Qing Wang
Summary: Incorporating two pyrrole subunits at the bay positions of perylene-diimide, PDI-2N, with a bowl depth of 1.52 angstrom, was successfully synthesized via one step Buchwald-Hartwig reaction. Despite the electron-rich pyrrole embedding, the radical anion and dianion of PDI-2N were easily prepared and investigated experimentally and theoretically. Furthermore, PDI-2N crystallized in different manners under distinct conditions, forming tubular crystals with infinite two-directional columnar stacking under DMF conditions. This discovery presents a promising bowl-shaped PDI derivative for organoelectronics.
Article
Chemistry, Physical
Chenjian Lin, Yue Qi, Paige J. Brown, Malik L. Williams, Jonathan R. Palmer, Michele Myong, Xingang Zhao, Ryan M. Young, Michael R. Wasielewski
Summary: This article studies the singlet fission (SF) phenomenon of perylene-3,4-dicarboximide (PMI) molecules in the solid state, and finds that 2,5-diphenyl-N-(2-ethylhexyl)perylene-3,4-dicarboximide (dp-PMI) is well-suited for the fission reaction, with high triplet yield and photostability, making it an attractive material for enhancing solar cell efficiency.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Physical
Jeswin Sunny, Ebin Sebastian, Suvarna Sujilkumar, Frank Wuerthner, Bernd Engels, Mahesh Hariharan
Summary: This study reports the unprecedented population of triplet excited states in a series of nitrogen-annulated perylene bisimide chromophores. Ultrafast intersystem crossing is found in Br-NPBI, leading to enhanced triplet population. The quantum chemical calculations reveal the important role of nitrogen annulation in tuning the excited state energy levels to favor intersystem crossing.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Organic
Oliver Nagler, Kazutaka Shoyama, Olga Anhalt, Matthias Stolte, Rajeev K. Dubey, Zengqi Xie, Frank Wuerthner
Summary: In this study, a new synthetic strategy was reported to control the structural and fluorescence properties of perylene bisimide (PBI) dyes by employing a 1,12-bay-substitution pattern. Novel perylene dyes with excellent structural and optical properties were successfully obtained through further functionalization of 1,12-dihydroxy-PBI derivatives.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Chris Rehhagen, Shahnawaz Rafiq, Kyra N. Schwarz, Gregory D. Scholes, Stefan Lochbrunner
Summary: Exciton migration is a crucial process for light harvesting in organic systems, but it is often hindered by the formation of trap states. In this study, the mobility of singlet and excimer excitons in nanoparticles made of perylene bisimide molecules was compared. The results showed that the mobility of excimer excitons can be higher than that of singlet excitons, and it is influenced by the intermolecular electronic coupling.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Applied
Sachin D. Padghan, Min-Chieh Chung, Qi-Sheng Zhang, Wei-Chun Lin, Kew-Yu Chen
Summary: In this study, a series of perylene bisimide compounds with different substituents were synthesized. The substituents were found to affect the absorption and fluorescence wavelengths of the compounds. One compound also exhibited colorimetric and turn-on fluorescence responses under extremely acidic conditions.
Article
Multidisciplinary Sciences
Ningning Tang, Jiadong Zhou, Liangxuan Wang, Matthias Stolte, Guojing Xie, Xinbo Wen, Linlin Liu, Frank Wuethner, Johannes Gierschner, Zengqi Xie
Summary: Nano-sized PBI dyes achieve deep-red emission and avoid common quenching pathways by tuning the dihedral angle between the aromatic and alkoxy groups.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Ilias Papadopoulos, David Gutierrez-Moreno, Yifan Bo, Ruben Casillas, Phillip M. Greissel, Timothy Clark, Fernando Fernandez-Lazaro, Dirk M. Guldi
Summary: In this study, a series of phenylene- and naphthalene-linked dimers were designed and synthesized to investigate the inherent differences in monoimide and diimide perylenes and their impact on singlet fission. The results showed that using naphthalene spacers improves the triplet quantum yield and singlet fission performance of both monoimide and diimide perylene derivatives.
Article
Chemistry, Organic
Yuki Tanaka, Kyohei Matsuo, Hiroko Yamada, Norihito Fukui, Hiroshi Shinokubo
Summary: Preparation of organic semiconductors by solution processes is desirable for flexible electronic devices. Our group reported new soluble precursors that can be transformed into n-type organic semiconductors through heating or light-irradiation. We developed a second-generation synthetic route to enable large-scale and diverse preparation of various N-substituted DNTBIs and identified suitable combinations of leaving group, external stimulus, and N-substituent for efficient charge transport.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Toyotaka Nakae, Masaki Nishio, Tsukasa Usuki, Minako Ikeya, Chika Nishimoto, Suguru Ito, Hiroshi Nishihara, Mineyuki Hattori, Shigenobu Hayashi, Teppei Yamada, Yoshinori Yamanoi
Summary: A sigma-pi extended aryldisilane with a thienopyrazine acceptor fragment and phenothiazine donor moiety was synthesized using Si-Si bridges, showing dual emission and fluorescence properties. Factors contributing to reversible fluorescence under external stimuli include packing mode, phenothiazine conformation variation, and morphological changes between crystalline and amorphous phases. Theoretical study revealed distinct conformational groups with slight energy differences, with the crystalline state promoting HOMO-LUMO separation. The proposed strategy offers guidance for developing stimuli-responsive materials with controlled excited states.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Chaochao Qin, Zheng Zhang, Qiaoling Xu, Jian Song, Zhaoyong Jiao, Shuhong Ma, Ruiping Qin, Yuhai Jiang
Summary: A J-type dimer PMI-2 was studied to investigate its excited-state dynamics. The results showed that a symmetry-breaking charge separation process in PMI-2 is mediated by a mixed excimer, which is a combination of localized Frenkel excitation and interunit charge transfer states. The transformation from a mixed state to the charge transfer state was found to be accelerated with increasing solvent polarity, accompanied by a significant reduction in the recombination time. Theoretical calculations revealed that these changes were attributed to the more negative free energy and lower energy levels of the charge transfer state in highly polar solvents. Our findings highlight the solvent-dependent charge separation process in J-type dimers.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Article
Chemistry, Organic
Yongjie Zhang, Siyuan Yuan, Ping Liu, Lei Jing, Hongfei Pan, Xiang-Kui Ren, Zhijian Chen
Summary: Two new boron-dipyrromethene (BODIPY) dyes, bearing uracil units and solubilizing alkyne groups, were synthesized and characterized. They were found to supramolecularly polymerize into J-aggregates in nonpolar solvents, demonstrating outstanding optical properties. The bulky alkyne substituents effectively hindered close contact between the pi-faces of BODIPY chromophores, leading to crucial segregation of supramolecular polymer chains for aggregation-induced emission enhancement (AIEE).
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Multidisciplinary Sciences
Jianyu Zhang, Parvej Alam, Siwei Zhang, Hanchen Shen, Lianrui Hu, Herman H. Y. Sung, Ian D. Williams, Jianwei Sun, Jacky W. Y. Lam, Haoke Zhang, Ben Zhong Tang
Summary: Researchers have designed clusteroluminogens that exhibit multiple emissions and white-light emission in the crystalline state by manipulating through-space interactions. The intensity ratio of these emissions can be easily controlled by changing the halide atom and excitation wavelength.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Ruchika Mishra, S. Sujesh, V. S. Archana, Ayushi Kaushik, Gaurav Gupta, Rahul Singhal, Ganesh D. Sharma, Jeyaraman Sankar
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Physics, Multidisciplinary
Jooyoung Sung, Christoph Schnedermann, Limeng Ni, Aditya Sadhanala, Richard Y. S. Chen, Changsoon Cho, Lee Priest, Jong Min Lim, Hyun-Kyung Kim, Bartomeu Monserrat, Philipp Kukura, Akshay Rao
Article
Chemistry, Applied
Hoa Thi Bui, Jong Min Lim, Duy Khuong Mai, Heemon Kim, Ho-Joong Kim, Hyung Jin Kim, Sung Cho
Article
Chemistry, Physical
Youngjin Choi, Sohee Lim, Joong Won Shim, Bonghwan Chon, Jong Min Lim, Minhaeng Cho
JOURNAL OF PHYSICAL CHEMISTRY B
(2020)
Article
Pharmacology & Pharmacy
Eline Boel, Piyush Panini, Guy Van den Mooter
Article
Chemistry, Physical
Saptarsi Mondal, Jooyoun Kang, Kwanghee Park, Jong Min Lim, Jeong-Hyon Ha, Kyungwon Kwak, Minhaeng Cho
Summary: The study reveals that water molecules adsorbed on highly biocompatible and poorly biocompatible acrylate-based polymers have different vibrational lifetimes, with PMEA showing stronger H-bonding interaction with water and PPEA exhibiting notably longer OD stretch vibrational lifetime. The results also demonstrate substantial spatial overlap between polymer CO group and water for hydrated PMEA, as well as a significant difference in surface morphology compared to PPEA, highlighting the underlying relationships among polymer-water interaction, surface morphology, and biocompatibility.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Organic
Shivangee Jha, Kundan Singh Mehra, Avantika Hasija, Deepak Chopra, Ramprasad Regar, Jeyaraman Sankar
Summary: A simple synthesis method is proposed to obtain previously unknown dibromo and tribromo rylenediimides, demonstrating their structural characteristics and the importance of bromo derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Materials Science, Biomaterials
Isabel Wen Badon, Chanwoo Kim, Jong Min Lim, Duy Khuong Mai, Temmy Pegarro Vales, Dongho Kang, Sung Cho, Joomin Lee, Ho-Joong Kim, Jaesung Yang
Summary: A series of cationic photosensitizers with mitochondrion-targeting properties were synthesized. The addition of bromine atoms in the photosensitizers increased the singlet oxygen quantum yield. The photosensitizers exhibited low cytotoxicity in the dark and high phototoxicity under light conditions.
JOURNAL OF MATERIALS CHEMISTRY B
(2022)
Article
Chemistry, Multidisciplinary
Kundan Singh Mehra, Shivangee Jha, Subhrajyoti Bhandary, Dipendranath Mandal, Ruchika Mishra, Jeyaraman Sankar
Summary: This article presents a simple and exciting strategy to synthesize novel terrylene diimide derivatives with absorption and intense emission in the near-IR through precise functionalization. The symmetrically substituted terrylene diimides show impressive emission quantum yields, and minimal structural distortion is found to be correlated with the emission characteristics. Additionally, a two-tiered TDI-carbazole compound with intense emission in the near-IR is reported.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Piyush Panini, Eline Boel, Luc Van Meervelt, Guy Van den Mooter
Summary: The phenomenon of solvatomorphism in drugs has significant implications in the pharmaceutical industry and crystal engineering. This study presents the crystal structure of Miconazole and its solvates, along with a detailed analysis of their packing using various methods.
CRYSTAL GROWTH & DESIGN
(2022)
Article
Chemistry, Multidisciplinary
Kundan Singh Mehra, Shivangee Jha, Anila M. Menon, Deepak Chopra, Jeyaraman Sankar
Summary: Here, we report the first examples of air-stable, deep-lowest unoccupied molecular orbital (LUMO) polycyclic aromatic molecules with emission in the near-infrared (NIR) region, achieved through nitration. Despite the non-emissive nature of nitroaromatics, the choice of a relatively electron-rich terrylene core allowed for fluorescence in these molecules. The degree of nitration directly influenced the stability of the LUMOs. The tetra-nitrated terrylene diimide exhibited the lowest LUMO (<=-4.5 eV) of -5.0 eV vs. Fc/Fc(+), making it the lowest among larger RDIs. These are also the only examples of emissive nitro-RDIs, with larger quantum yields.
Article
Chemistry, Analytical
Chanjong Park, Jong Min Lim, Seok-Cheol Hong, Minhaeng Cho
Summary: Infrared photothermal microscopy is a non-invasive and label-free imaging technique that has been used in various research areas. However, the narrow spectral width of the preferred excitation light source limits the molecular information obtained. Here, we introduce a two-color IR photothermal microscopy technique that overcomes this limitation and allows for the imaging and differentiation of two chemical species in live cells.
Article
Chemistry, Inorganic & Nuclear
Amit Kumar, S. Sujesh, Prachi Varshney, Amit Paul, Sankar Jeyaraman
DALTON TRANSACTIONS
(2019)