Erik Budi Santiko, Shrestha Binod Babu, Fan Zhang, Cheng-Lin Wu, Tzu-Chau Lin, Manabu Abe
A new cyclic 1 stilbene derivative, 6-(4-(diphenylamino)phenyl)-N,N-diphenyl-7,8-dihydronaphthalen-2-amine (D2PDN), featuring quadrupolar system having electron-donating substituents (NPh2), was synthesized and characterized in this study. The fluorescence quantum yield was 89% (under air) and 99% (under argon) in toluene. The two-photon (2P) cross-section was determined to be 166 GM at 700 nm using 2P-excitation fluorescence method. The 2P-responsive chromophore in near-infrared region has reversible oxidation signals at 0.17, 0.28, and 0.53 V vs Fc0/Fc+. Compound D2PDN, E*ox = –2.83 V, was found to be used as a simultaneous 2P-responsive photoredox catalyst. A new cyclic stilbene derivative, 6-(4-(diphenylamino)phenyl)-N,N-diphenyl-7,8-dihydronaphthalen-2-amine (D2PDN) was synthesized and characterized. The fluorescence quantum yield was 99% under Argon in toluene. The two-photon (2P) cross-section was determined to be 166 GM at 700 nm. The 2P-responsive chromophore has reversible oxidation potentials at 0.17, 0.28, and 0.53 V vs Fc0/Fc+. D2PDN was found to be used as a photoredox catalyst.
合成了一种新的环苯乙烯衍生物6-(4-(二苯基氨基)苯基)- n, n-二苯基-7,8-二氢萘-2-胺(D2PDN)，具有四极性供电子取代基(NPh2)体系。在甲苯中，荧光量子产率分别为89%(空气)和99%(氩气)。用2P激发荧光法测定了700 nm处的双光子(2P)截面为166 GM。在近红外区，2p响应的发色团在0.17、0.28和0.53 V vs Fc0/Fc+时具有可逆的氧化信号。化合物D2PDN, E*ox = -2.83 V，可作为同时响应2p的光氧化还原催化剂。合成了一种新的环苯乙烯衍生物6-(4-(二苯胺)苯基)- n, n-二苯基-7,8-二氢萘-2-胺(D2PDN)。在甲苯氩气条件下，荧光量子产率达99%。在700 nm处测得双光子(2P)截面为166 GM。在f0 /Fc+下，2p响应色团的氧化电位分别为0.17、0.28和0.53 V。发现D2PDN可作为光氧化还原催化剂。
{"title":"Synthesis, Characterization, and Application of a Cyclic Stilbene Derivative with Simultaneous Two-Photon Absorption Character","authors":"Erik Budi Santiko, Shrestha Binod Babu, Fan Zhang, Cheng-Lin Wu, Tzu-Chau Lin, Manabu Abe","doi":"10.1246/cl.230388","DOIUrl":"https://doi.org/10.1246/cl.230388","url":null,"abstract":"A new cyclic 1 stilbene derivative, 6-(4-(diphenylamino)phenyl)-N,N-diphenyl-7,8-dihydronaphthalen-2-amine (D2PDN), featuring quadrupolar system having electron-donating substituents (NPh2), was synthesized and characterized in this study. The fluorescence quantum yield was 89% (under air) and 99% (under argon) in toluene. The two-photon (2P) cross-section was determined to be 166 GM at 700 nm using 2P-excitation fluorescence method. The 2P-responsive chromophore in near-infrared region has reversible oxidation signals at 0.17, 0.28, and 0.53 V vs Fc0/Fc+. Compound D2PDN, E*ox = –2.83 V, was found to be used as a simultaneous 2P-responsive photoredox catalyst. A new cyclic stilbene derivative, 6-(4-(diphenylamino)phenyl)-N,N-diphenyl-7,8-dihydronaphthalen-2-amine (D2PDN) was synthesized and characterized. The fluorescence quantum yield was 99% under Argon in toluene. The two-photon (2P) cross-section was determined to be 166 GM at 700 nm. The 2P-responsive chromophore has reversible oxidation potentials at 0.17, 0.28, and 0.53 V vs Fc0/Fc+. D2PDN was found to be used as a photoredox catalyst.","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":"58 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135342863","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Gelation of a hydrophilic polymer bearing a metal-coordination unit with various metal ions was examined. Gels with different morphologies were formed depending on the metal ion species. The formation mechanism for these gels could be explained based on their cross-linking rates. Gelation in two-component solutions containing different ratios of PdII to other metal ions (AuIII and PtIV) was also investigated. Gelation of a hydrophilic polymer bearing a metal-coordination unit with various metal ions was examined. Gels with different morphologies were formed depending on the metal ion species. The formation mechanism for these gels could be explained based on their cross-linking rates. Gelation in two-component solutions containing different ratios of PdII to other metal ions (AuIII and PtIV) was also investigated.
{"title":"Gelation of Hydrophilic Polymer Bearing Metal-Coordination Unit with Various Metal Ions","authors":"Daisuke Nagai, Naoki Isobe, Yasuyuki Maki, Shusuke Okamoto","doi":"10.1246/cl.230347","DOIUrl":"https://doi.org/10.1246/cl.230347","url":null,"abstract":"Gelation of a hydrophilic polymer bearing a metal-coordination unit with various metal ions was examined. Gels with different morphologies were formed depending on the metal ion species. The formation mechanism for these gels could be explained based on their cross-linking rates. Gelation in two-component solutions containing different ratios of PdII to other metal ions (AuIII and PtIV) was also investigated. Gelation of a hydrophilic polymer bearing a metal-coordination unit with various metal ions was examined. Gels with different morphologies were formed depending on the metal ion species. The formation mechanism for these gels could be explained based on their cross-linking rates. Gelation in two-component solutions containing different ratios of PdII to other metal ions (AuIII and PtIV) was also investigated.","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":"18 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135344093","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
After subjecting a hydrofluoric acid treated and annealed TiO2(110) single-crystal substrate to immersion in an ethanol solution of aniline, a uniform step structure in the [001] direction was observed on the TiO2(110) surface without aniline. Since this finding is considered to control of the step direction on the TiO2(110) surface, the formed surface was discussed in detail and a model of the step line formation process was proposed. After immersing of TiO2(110) single-crystal substrate in an ethanol solution containing aniline, a uniform step structure in the [001] direction formed on the TiO2(110) surface although aniline was not existed. A reasonable model of the step line formation process was proposed. The present results lead to the novel method to control of the step direction on the TiO2(110) surface.
{"title":"Etching of TiO<sub>2</sub>(110) Single-Crystal Surface with Aniline for Step Direction Control","authors":"Mami Takahari, Taiga Goto, Soichiro Yoshimoto, Toshihiro Kondo","doi":"10.1246/cl.230334","DOIUrl":"https://doi.org/10.1246/cl.230334","url":null,"abstract":"After subjecting a hydrofluoric acid treated and annealed TiO2(110) single-crystal substrate to immersion in an ethanol solution of aniline, a uniform step structure in the [001] direction was observed on the TiO2(110) surface without aniline. Since this finding is considered to control of the step direction on the TiO2(110) surface, the formed surface was discussed in detail and a model of the step line formation process was proposed. After immersing of TiO2(110) single-crystal substrate in an ethanol solution containing aniline, a uniform step structure in the [001] direction formed on the TiO2(110) surface although aniline was not existed. A reasonable model of the step line formation process was proposed. The present results lead to the novel method to control of the step direction on the TiO2(110) surface.","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":"34 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135477192","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Hainan Sun, Yingying Wang, Xiangan Meng, Manman Hu, Xin Yan
{"title":"Unraveling the Interactions between Nanoparticles and Benzo[a]pyrene in Environmental Waters and Human Blood by Dissipative Particle Dynamics Simulations","authors":"Hainan Sun, Yingying Wang, Xiangan Meng, Manman Hu, Xin Yan","doi":"10.1246/cl.230337","DOIUrl":"https://doi.org/10.1246/cl.230337","url":null,"abstract":"","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":"332 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136010428","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Thermal stability plays a crucial role in determining the polymer suitability as high-performance thermoresistant materials, which are highly demanded for lightweight substitute to metal or ceramic materials in a sustainable society. We here present an innovative approach involving the in-situ substitution of imidazole protons of polybenzimidazole (PBI) derivatives with deuterium using deuterated solvents to enhance thermal stability. The resulting substituted polymers exhibited significantly higher thermal decomposition temperatures compared to their original counterparts. This notable improvement can be attributed to the N-D bond, which possesses a low stretching frequency, demanding a greater amount of activating energy compared to the N-H bond, enabling the polymer to withstand higher temperatures. This discovery presents a novel and promising avenue for enhancing polymer thermoresistance, providing valuable insights for the development of advanced materials with enhanced thermal stability. Pinpoint surgery through in situ isotopic proton-deuterium substitution significantly enhanced the thermal degradation temperature of polybenzoxazoles, this is because N-D bond exhibit a lower stretching frequency than N-H, demanding more activating energy and thus can withstand higher temperature. This discovery provides a novel and straightforward method to elevate thermostability for polymers.
{"title":"Pin-point surgery of proton-deuterium substitution to enhance polybenzimidazole thermoresistances","authors":"Xianzhu Zhong, Aniruddha Nag, Jiabei Zhou, Kenji Takada, Motoyuki Kusano, Tatsuo Kaneko","doi":"10.1246/cl.230315","DOIUrl":"https://doi.org/10.1246/cl.230315","url":null,"abstract":"Thermal stability plays a crucial role in determining the polymer suitability as high-performance thermoresistant materials, which are highly demanded for lightweight substitute to metal or ceramic materials in a sustainable society. We here present an innovative approach involving the in-situ substitution of imidazole protons of polybenzimidazole (PBI) derivatives with deuterium using deuterated solvents to enhance thermal stability. The resulting substituted polymers exhibited significantly higher thermal decomposition temperatures compared to their original counterparts. This notable improvement can be attributed to the N-D bond, which possesses a low stretching frequency, demanding a greater amount of activating energy compared to the N-H bond, enabling the polymer to withstand higher temperatures. This discovery presents a novel and promising avenue for enhancing polymer thermoresistance, providing valuable insights for the development of advanced materials with enhanced thermal stability. Pinpoint surgery through in situ isotopic proton-deuterium substitution significantly enhanced the thermal degradation temperature of polybenzoxazoles, this is because N-D bond exhibit a lower stretching frequency than N-H, demanding more activating energy and thus can withstand higher temperature. This discovery provides a novel and straightforward method to elevate thermostability for polymers.","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":"18 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136010427","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Structure Identification of Dynamic Zinc(II)-Ligand Assemblies in Solution Based on Ligand Chirality","authors":"Daiji Ogata, Junpei Yuasa","doi":"10.1246/cl.230353","DOIUrl":"https://doi.org/10.1246/cl.230353","url":null,"abstract":"","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":"203 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135354293","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
The Scholl reactions of di(1-anthryl) ketones were performed with chloranil under an acidic condition. The reaction of the parent ketone gave a cyclized product containing a seven-membered ring, which was enantiomerically separable. In contrast, the reaction of 4-(mesityloxy)-1-anthryl derivative mainly afforded an unexpected polycyclic aromatic ketone consisting of eight six-membered rings via skeletal rearrangement. The structure and properties of these products and the reaction mechanism are reported. Two di(1-anthryl) ketones gave different dehydrocyclization products upon treatment with chloranil. In particular, the (2,4,6-trimethylphenyl)oxy substituted derivative produced a novel aromatic ketone via unexpected skeletal rearrangement. This result is in contrast to that of the substituent free derivative, which formed a simple cyclization product with a helical structure.
{"title":"Formation of Novel Polycyclic Aromatic Compounds by Scholl Reactions of Di(1-anthryl) Ketones via Cyclization and Rearrangement","authors":"Shinji Toyota, Hiroshi Sekikawa, Hiroki Fukuda, Hiroshi Ikeda, Eiji Tsurumaki","doi":"10.1246/cl.230340","DOIUrl":"https://doi.org/10.1246/cl.230340","url":null,"abstract":"The Scholl reactions of di(1-anthryl) ketones were performed with chloranil under an acidic condition. The reaction of the parent ketone gave a cyclized product containing a seven-membered ring, which was enantiomerically separable. In contrast, the reaction of 4-(mesityloxy)-1-anthryl derivative mainly afforded an unexpected polycyclic aromatic ketone consisting of eight six-membered rings via skeletal rearrangement. The structure and properties of these products and the reaction mechanism are reported. Two di(1-anthryl) ketones gave different dehydrocyclization products upon treatment with chloranil. In particular, the (2,4,6-trimethylphenyl)oxy substituted derivative produced a novel aromatic ketone via unexpected skeletal rearrangement. This result is in contrast to that of the substituent free derivative, which formed a simple cyclization product with a helical structure.","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":"58 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135824872","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Based on the self-assembling amphiphilic peptide GAVILRR, we developed a peptide amphiphile bearing octanoyl and octaarginine groups that formed stable nanoparticles with siRNA delivery capabilities. The N-terminal addition of an octanoyl group reduced the particle size and polydispersity. The C-terminal polyarginine extension allowed the formation of nanoparticles with greater stability and smaller sizes with siRNA loading compared to those for the original and other variant peptides. The resulting peptide amphiphile PA8 effectively delivered siRNA into AsPC-1 pancreatic cancer cells. We developed a peptide amphiphile (PA) consisting of a hydrophobic alkyl chain, a hydrophobic GAVIL peptide, and a hydrophilic polyarginine. The existence of an alkyl chain promoted the self-assembly of PA to form nanoparticles. To the surface of nanoparticles, siRNA could be attached, producing positively charged nanocomplexes that effectively internalize into cancer cells.
{"title":"Self-assembly of Peptide Amphiphiles with Alkyl Groups for siRNA Delivery","authors":"Taufik F.N. Hakim, Kazunori Watanabe, Shomu Fujimoto, Mizuki Kitamatsu, Takashi Ohtsuki","doi":"10.1246/cl.230302","DOIUrl":"https://doi.org/10.1246/cl.230302","url":null,"abstract":"Based on the self-assembling amphiphilic peptide GAVILRR, we developed a peptide amphiphile bearing octanoyl and octaarginine groups that formed stable nanoparticles with siRNA delivery capabilities. The N-terminal addition of an octanoyl group reduced the particle size and polydispersity. The C-terminal polyarginine extension allowed the formation of nanoparticles with greater stability and smaller sizes with siRNA loading compared to those for the original and other variant peptides. The resulting peptide amphiphile PA8 effectively delivered siRNA into AsPC-1 pancreatic cancer cells. We developed a peptide amphiphile (PA) consisting of a hydrophobic alkyl chain, a hydrophobic GAVIL peptide, and a hydrophilic polyarginine. The existence of an alkyl chain promoted the self-assembly of PA to form nanoparticles. To the surface of nanoparticles, siRNA could be attached, producing positively charged nanocomplexes that effectively internalize into cancer cells.","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":"26 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135824873","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kehan Cheng, Ken-ichi Shinohara, Koichi Higashimine, M. Teraguchi, T. Kaneko, T. Aoki
{"title":"Synthesis of two-dimensional multi-functional macromonomer and oxygen permselectivity of its supramolecular and covalent polymer membranes","authors":"Kehan Cheng, Ken-ichi Shinohara, Koichi Higashimine, M. Teraguchi, T. Kaneko, T. Aoki","doi":"10.1246/cl.230341","DOIUrl":"https://doi.org/10.1246/cl.230341","url":null,"abstract":"","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":" ","pages":""},"PeriodicalIF":1.6,"publicationDate":"2023-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44173098","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Copper-mediated Trifluoromethylthiolation of Alkenyl Iodides with AgSCF3","authors":"Yuki Kojima, K. Hirano","doi":"10.1246/cl.230335","DOIUrl":"https://doi.org/10.1246/cl.230335","url":null,"abstract":"","PeriodicalId":9862,"journal":{"name":"Chemistry Letters","volume":" ","pages":""},"PeriodicalIF":1.6,"publicationDate":"2023-09-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42588475","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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