1640-39-7Relevant academic research and scientific papers
Study on the synthesis and spectra of a novel kind of carbozole benzothiazole indole styryl cyanine dye with a carbazole bridged Chain
Fei, Xuening,Hao, Yachao,Gu, Yingchun,Li, Chao,Yu, Lu
, p. 563 - 568 (2014)
Based on the frequently-used cyanine dye probe thiazole orange (TO) and Cy3, a novel kind of styryl cyanine dye was designed and synthesized. Carbazole was inserted into the structures of two cyanine dyes, TO and Cy3, to act as a bridge to link the benzothiazole and indole. This modification resulted in a novel kind of carbozole benzothiazole indole cyanine dye with a carbazole-bridged chain. The dyes were characterized by HNMR and MS. The spectra of the novel dyes were also studied and the results showed that the fluorescence wavelength of novel carbazole benzothiazole indole cyanine dye shifted red, the Stokes shift and Fluorescence quantum yields increased and the fluorescence intensity was enhanced compared to that of TO. These results indicated that the novel dye could be used as an excellent fluorescent probe in biological labeling.
The effect of bis-carboxylic groups of squarylium dyes on the efficiency of dye-sensitized solar cells
Al-horaibi, Sultan A.,Garoon, Eman M.,Bhise, Narendra A.,Gaikwad, Suresh T.,Rajbhoj, Anjali S.
, p. 1769 - 1778 (2020)
Symmetric squarylium dye (SQIND1) with bi-carboxylic groups has been synthesized and photoelectrochemical properties have been studied in comparison with its non-functionalized analog groups (SQIND2). The experimental results showed that the introduction of anchor carboxylic groups in SQIND1 sensitizer provides a more intimate contact with nanoparticles TiO2 which increases the number of charge carriers transferred from the SQIND1 to the semiconductor. The theoretical calculations and absorbance results show that the electron density of LUMO of SQIND1 is delocalized in the whole chromophore, leading to strong electronic coupling between SQIND1 sensitizer and conducting band of TiO2, resulting in improved dye-sensitized solar cell efficiency compared to SQIND2. Hence, the SQIND1 sensitized exhibit better photovoltaic performance. Although, the absence of any linker groups in the SQIND1, then SQIND1 was perfect efficiently sensitized on porous TiO2 with the long UV–Vis and NIR region up to 800?nm of the spectrum and showed higher remarkable performance of values, such as η of 3.3%, a Jsc of 7.6?mA/cm2, a Voc of 0.59, and FF of 0.73.
Benz[c,d]indolium-containing monomethine cyanine dyes: Synthesis and photophysical properties
Soriano, Eduardo,Holder, Cory,Levitz, Andrew,Henary, Maged
, (2016)
Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.
A carbazole-hemicyanine dye based ratiometric fluorescent probe for selective detection of bisulfite (HSO3 ?) in cells and C. elegans
Bi, Keying,Tan, Rui,Hao, Ruiting,Miao, Lanxi,He, Yanqi,Xianghua, Wu,Zhang, Junfeng,Rui, Xu
, p. 545 - 548 (2019)
Bisulfite (HSO3 ?) is an important sulfur dioxide (SO2) derivative, which plays a major role in many physiological processes and is also closely associated with a variety of diseases. Thus the development of highly selective and sensitive fluorescent probes is essential to detect HSO3ˉ in living cells. In this work, we report the synthesis and analysis of a ratiometric fluorescent probe for selective detection of HSO3ˉ based on the 1,4-nucleophilic addition reaction with the carbazole as an electron donor (D) and aldehyde group as an electron acceptor (A). The addition of HSO3ˉ and other ions to our probe can be observed by UV - vis and fluorescence spectrometry. Our investigation proved that the probe is highly selective and sensitive for HSO3ˉ and ratiometric changes. Moreover, the probe has good cell permeability and was successfully applied to the detection of exogenous HSO3ˉ in Hela cells and C. elegans.
Ultrabright and Serum-Stable Squaraine Dyes
Yadav, Yogesh,Owens, Eric,Nomura, Shinsuke,Fukuda, Takeshi,Baek, Yoonji,Kashiwagi, Satoshi,Choi, Hak Soo,Henary, Maged
, p. 9436 - 9445 (2020)
Highly stable symmetric and asymmetric squaraine fluorophores have been synthesized featuring an internal salt bridge between a quaternary ammonium cation and the central oxycyclobutenolate ring of the chromophore. Some of our newly synthesized symmetric and asymmetric compounds display increased molar absorptivity, quantum yield in serum, and thermal/photochemical stability over previously reported squaraine-based dyes. Consequently, both classes show great promise in resurfacing the normal environment-labile squaraine dyes as novel imaging agents and scaffolds for fluorescence sensing. Furthermore, incorporating a covalent attachment point away from the conjugated system allows for biological tagging applications without disturbing the optimum optical characteristics of the newly designed fluorophore.
Photophysical characterization and BSA interaction of the direct ring carboxy functionalized unsymmetrical NIR cyanine dyes
Saikiran, Maryala,Sato, Daisuke,Pandey, Shyam S.,Ohta, Takeshi,Hayase, Shuzi,Kato, Tamaki
, p. 6 - 13 (2017)
Novel near infrared (NIR) sensitive unsymmetrical cyanine dyes bearing direct –COOH functionalized indole ring were synthesized, characterized and subjected to photophysical investigations. These unsymmetrical cyanine dyes were then subjected to investigate their interaction with bovine serum albumin (BSA) as a model protein in Phosphate buffer solutions. Apart from NIR absorption and emission with high molar extinction coefficients they exhibit a blue shift in PBS solution owing to their enhanced dye aggregation. Interaction of these dyes with BSA leads to not only enhanced emission intensity but also bathochromically shifted absorption maximum due to formation of dye-BSA conjugate. These dyes bind strongly with BSA having about an order of magnitude higher binding constant as compared to the typical cyanine dyes. Amongst the unsymmetrical cyanine dyes investigated in this work one bearing substituents like Iodo and carboxylic acid in the terminal Indole rings (UCD-3) exhibited highest association with the BSA having very high binding constant of 1.01?×?107?M?1.
An indocyanine-based turn-on fluorescent probe for specific detection of biothiols
Wang, Xiaojing,Jin, Di,Li, Xue,Yan, Xilong,Wang, Bowei
, p. 707 - 715 (2018)
A novel heptamethine cyanine-based turn-on fluorescent probe Cy-DNBS was designed and synthesized, which was used successfully to detect biothiols with high selectivity and sensitivity. With the addition of biothiols, the probe displayed ~30-fold fluorescence enhancement at 625 nm. Meanwhile, the solution color changed remarkably from green to red, which provides a method to recognize biothiols by the ‘naked eye’. The detection limit of Cys, GSH and Hcy are 2.24 nM, 1.99 nM and 4.46 nM, respectively.
Near-infrared squaraine fluorescent probe for imaging adenosine 5′-triphosphate in live cells
Wang, Guimei,Jiang, Xiaoxue,Fu, Nanyan
, (2019)
Adenosine 5′-triphosphate (ATP), as a “molecular currency” for intracellular energy transfer, not only participates in various physiological activities, but also involves in various pathological processes of living cells. Therefore, the establishment of a simple, rapid, sensitive and accurate ATP analysis method is of great significance for the study of its physiological functions. In this work, we rationally design a near-infrared phenylboronic acid group-functionalized dicyanovinyl squaraine (SQ-PBA3), with which a supramolecular assembly was constructed for fluorescent imaging of ATP. In PBS buffer, SQ-PBA3 changes self-assembly when adding cetyltrimethyl ammonium bromide (CTAB) deriving fluorescence response of SQ-PBA3 to ATP with the maximum emission at 700 nm, due to the specificity of phenylboronic acid to diols and the multiple electrostatic interactions between SQ-PBA3, ATP and CTAB molecules. Meanwhile, the probe was successfully applied to monitor intracellular ATP level in MCF-7 cells with high sensitivity and selectivity.
Photochromism of neutral spiropyran in the crystalline state at room temperature
Fang, Bing,Li, Pengyu,Wang, Qian,Wu, Zhen,Yin, Meizhen
, p. 6290 - 6296 (2021)
Solid-state photochromic materials are very attractive due to their promising future in advanced functional materials with reversible and tunable optical properties. However, the development of photochromic material in the solid state, especially in the crystalline state, is still a great challenge due to dense molecular packing. In this study, a solid-state optical switch based on the methanol-esterified spiropyran derivative S1 is constructed, which exhibits reversible photochromic properties in the solid-state product without further recrystallization. Moreover, the cultured single crystal (S1-C) can unexpectedly undergo photochromism at room temperature, which is a very rare example in a neutral spiropyran crystal. The crystallographic analysis reveals that weak van der Waals forces dominate in the crystal of S1-C, resulting in a relatively loose packing mode and photochromic properties. Mechanical force can destroy the restricted environment of the crystalline state and allow the S1 compound to achieve more efficient photochromism. Our study opens up an avenue for relating the molecular structure/packing mode to photochromic properties. Consequently, by utilizing the reversible and efficient photochromic properties, we successfully demonstrate the application of S1 as optical printing materials. This journal is
Squaraine-based polymer dots with narrow, bright near-infrared fluorescence for biological applications
Wu, I-Che,Yu, Jiangbo,Ye, Fangmao,Rong, Yu,Gallina, Maria Elena,Fujimoto, Bryant S.,Zhang, Yong,Chan, Yang-Hsiang,Sun, Wei,Zhou, Xing-Hua,Wu, Changfeng,Chiu, Daniel T.
, p. 173 - 178 (2015)
This article describes the design and development of squaraine-based semiconducting polymer dots (Pdots) that show large Stokes shifts and narrow-band emissions in the near-infrared (NIR) region. Fluorescent copolymers containing fluorene and squaraine units were synthesized and used as precursors for preparing the Pdots, where exciton diffusion and likely through-bond energy transfer led to highly bright and narrow-band NIR emissions. The resulting Pdots exhibit the emission full width at half-maximum of ～36 nm, which is ～2 times narrower than those of inorganic quantum dots in the same wavelength region (～66 nm for Qdot705). The squaraine-based Pdots show a high fluorescence quantum yield (QY) of 0.30 and a large Stokes shift of ～340 nm. Single-particle analysis indicates that the average per-particle brightness of the Pdots is ～6 times higher than that of Qdot705. We demonstrate bioconjugation of the squaraine Pdots and employ the Pdot bioconjugates in flow cytometry and cellular imaging applications. Our results suggest that the narrow bandwidth, high QY, and large Stokes shift are promising for multiplexed biological detections.
