scholarly journals A Series of Imidazole Derivatives: Synthesis, Two-Photon Absorption, and Application for Bioimaging

2015 ◽  
Vol 2015 ◽  
pp. 1-8 ◽  
Author(s):  
Yingzhong Zhu ◽  
Lufei Xiao ◽  
Meng Zhao ◽  
Jiazheng Zhou ◽  
Qiong Zhang ◽  
...  

A new series of D-π-A type imidazole derivatives have been synthesized and characterized. Two corresponding imidazolium salts (iodine and hexafluorophosphate) were prepared from the imidazole compound. Their electron-withdrawing ability can be largely tunable by salt formation reaction or ion exchange. UV-vis absorption and single-photon fluorescence spectra have been systematically investigated in different solvents. The two-photon cross sectionsδ2PAof the imidazole derivatives are measured by two-photon excited fluorescence (2PEF) method. Compared with those ofT-1(107 GM) andT-3(96 GM),T-2(imidazolium iodine salt) has a large two-photon absorption (2PA) cross section value of 276 GM. Furthermore, the cytotoxicity and applications in bioimaging for the imidazole derivatives were carried out. The results showed thatT-1can be used as a lysosomal tracker with high stability and water solubility within pHs of 4–6, whileT-2andT-3can be used as probes for cell cytoplasm.

Absolute values of the two-photon absorption cross-sections of Rhodamine 6G, Rhodamine B, Acridine Red, Disodium Fluorescein and DODCI have been obtained by excitation with a neodymium: glass laser (1060 nm). Measurements over eight orders of magnitude of the exciting light flux were carried out by employing the laser both Q-switched and mode-locked. The two-photon fluorescence flux measurements were calibrated by single-photon fluorescence generated by excitation with second-harmonic laser pulses. The experimental results are compared with values predicted by semi-empirical theoretical models and good agreement is obtained. Two-photon amplification of the mode-locked neodymium laser by organic dyes is shown not to be practicable at present. Other possible two-photon oscillators are discussed.


2019 ◽  
Vol 955 ◽  
pp. 37-43
Author(s):  
Martin Vala ◽  
Matouš Kratochvíl ◽  
Patricie Heinrichova ◽  
Martin Weiter

The paper deals with determination of two-photon absorption cross-sections of selected representatives of diketo-pyrrolo-pyrrole. The materials were optimized in order to test the influence of various substitutions on the diketo-pyrrolo-pyrrole basic molecule. The two-photon absorption cross-sections were determined using two-photon excited fluorescence technique. A considerably high two-photon absorption cross-section in order of 1000 GM was found for non-symmetrically substituted derivative with donor-acceptor structure. All of the derivatives showed strong fluorescence in solid state visible by naked eye. These results demonstrate that this class of materials can be used in e.g. two-photon fluorescence microscopy in the form of nanoparticles.


2005 ◽  
Vol 70 (2) ◽  
pp. 201-208 ◽  
Author(s):  
L.U. Ping ◽  
Ming Xia

Three new thiophene based organic luminescence compounds, i.e., 2,5-bis(4?-N,N-dimethylaminostyryl) thiophene (BMST), 2,5-bis(4?-N,N-diethylaminostyryl)thiophene (BEST) and 2,5-bis(4?-N-cyclobutylaminostyryl)thiophene (BBST), were synthesized. All of their measured single-photon excited fluorescence (SPEF) are located in the range of ? 530 nm with quantum yields of around 40 %, and the corresponding lifetime was ? 1 ns. The examined compounds show strong solvatochromism in their SPEF spectra. Excited by a fs laser at 800 nm, a strong up-converted fluorescence of the examined compounds was detected. The profile of two-proton excited fluorescence (TPEF) was similar to that of SPEF. The two-photon absorption (TPA) cross sections of the compounds were determined by the TPEF method. All the compounds showed large TPA cross sections. Hence these thiophene derivatives may have good TPA properties.


Author(s):  
John V. Garcia ◽  
Fan Zhang ◽  
Peter C. Ford

Multi-photon excitation allows one to use tissue transmitting near-infrared (NIR) light to access excited states with energies corresponding to single-photon excitation in the visible or ultraviolet wavelength ranges. Here, we present an overview of the application of both simultaneous and sequential multi-photon excitation in studies directed towards the photochemical delivery (‘uncaging’) of bioactive small molecules such as nitric oxide (NO) to physiological targets. Particular focus will be directed towards the use of dyes with high two-photon absorption cross sections and lanthanide ion-doped upconverting nanoparticles as sensitizers to facilitate the uncaging of NO using NIR excitation.


2004 ◽  
Vol 82 (1) ◽  
pp. 19-26 ◽  
Author(s):  
Xin Zhou ◽  
Ai-Min Ren ◽  
Ji-Kang Feng ◽  
Xiao-Juan Liu

The one-photon absorption (OPA) properties of tetrabenzoporphyrins (TBPs) and phthalocyanines (Pcs) were studied using the semiempirical ZINDO method and time-dependent density functional theory (TDDFT), respectively. The compared results confirmed that the semiempirical ZINDO method was reasonably reliable when calculating the OPA of tetrabenzoporphyrins and phthalocyanines. On the basis of the OPA properties obtained from the ZINDO method, two-photon absorption (TPA) properties of two series of molecules were investigated, using ZINDO and sum-over-states (SOS) methods. The results showed that the TPA cross-sections of all molecules were in the range of 220.6 × 10–50 – 345.9 × 10–50 cm4·s·photon–1, which were in the same order of magnitude as the values reported in the literature. The relatively larger δ(ω) value for Pcs with respect to that for corresponding TBPs originates from larger intramolecular charge transfer, which can be characterized by the difference of dipole moment between S0 and S1 and the transition dipole moment between S1 and S5.Key words: two-photon absorption, ZINDO, sum-over-states, tetrabenzoporphyrin, phthalocyanines.


2006 ◽  
Vol 12 (8) ◽  
pp. 2303-2317 ◽  
Author(s):  
Shin-ichiro Kato ◽  
Taisuke Matsumoto ◽  
Motoyuki Shigeiwa ◽  
Hideki Gorohmaru ◽  
Shuuichi Maeda ◽  
...  

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