Aggregation-Induced Emission and Large Two-Photon Absorption Cross-Sections of Diketopyrrolopyrrole (DPP) Derivatives

2012 ◽  
Vol 65 (4) ◽  
pp. 387 ◽  
Author(s):  
Bing Wang ◽  
Nannan He ◽  
Bo Li ◽  
Shuangying Jiang ◽  
Yi Qu ◽  
...  
Keyword(s):  
Cross Section ◽  
Cross Sections ◽  
Photon Absorption ◽  
Attractive Alternative ◽  
Absorption Properties ◽  
Intramolecular Vibration ◽  
Symmetrical Structure ◽  
Aggregation Induced Emission ◽  
Two Photon Absorption ◽  
Two Photon

In this work, a new series of triphenylamine-based diketo-pyrrolo-pyrrole (DPP) compounds (DPP-I, DPP-II, DPP-III) have been designed and synthesized by a concise route. Their one- and two-photon absorption properties have been investigated. It was found that DPP-based compounds are very weakly fluorescent in THF solution, but their intensities are increased by almost 29, 9, and 24 times in water/THF (v/v 90 %) mixtures, respectively, in which they exhibit a strongly enhanced red fluorescence. The result indicates that the intramolecular vibration and rotation of these dyes is considerably restricted in nano-aggregates formed in water/THF mixtures, which leads to significant increases in fluorescence. The two-photon absorption (2PA) cross-sections measured by the open aperture Z-scan technique were determined to be 188, 275 and 447 GM for DPP-I, DPP-II, and DPP-III, respectively; DPP-III with the symmetrical structure shows the highest value of 2PA cross-section. The excellent properties of aggregation-induced emission (AIE) and 2PA provide an attractive alternative for the biophotonic materials.

Small molecules based on diphenylamine and carbazole with large two-photon absorption cross sections and extraordinary AIEE properties

RSC Advances ◽  
2014 ◽  
Vol 4 (73) ◽  
pp. 38939-38942 ◽  
Author(s):  
Guojian Tian ◽  
Wei Huang ◽  
Shengyun Cai ◽  
Haitao Zhou ◽  
Bo Li ◽  
...  
Keyword(s):  
Small Molecules ◽  
Cross Section ◽  
Cross Sections ◽  
Absorption Cross Section ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Aggregation Induced Emission ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Emission Enhancement

Two simple small molecules based on diphenylamine (T1) and carbazole (T2) have been synthesized and characterized. Both dyes exhibit extraordinary aggregation-induced emission enhancement properties and high corresponding quantum efficiencies of 11.5% and 16.0%. The value of the two-photon absorption cross-section for T1 is 1240 GM.

Substituent effects on the aggregation-induced emission and two-photon absorption properties of triphenylamine–dibenzo[a,c]phenazine adducts

2017 ◽  
Vol 1 (7) ◽  
pp. 1396-1405 ◽  
Author(s):  
Ji Yang ◽  
Yuting Gao ◽  
Tao Jiang ◽  
Wen Liu ◽  
Chenchen Liu ◽  
...  
Keyword(s):  
Substituent Effects ◽  
Photon Absorption ◽  
Absorption Properties ◽  
Aggregation Induced Emission ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Combined Features

Non-substituted and alkyl-substituted triphenylamine–dibenzo[a,c]phenazine adducts (Q1–Q3) showed the combined features of ICT plus AEE, while the alkoxy-substituted Q4–Q5 exhibited obvious AIE effects.

A small-molecule with a large two-photon absorption cross-section serves as a membrane-permeable ribonucleic acid (RNA) probe for live cell imaging

2018 ◽  
Vol 42 (17) ◽  
pp. 14325-14331 ◽  
Author(s):  
Ruiqing Feng ◽  
Longlong Li ◽  
Bing Li ◽  
Jinhui Li ◽  
Dan Peng ◽  
...  
Keyword(s):  
Cross Section ◽  
Cross Sections ◽  
Live Cell Imaging ◽  
Plasma Membranes ◽  
Cell Imaging ◽  
Photon Absorption ◽  
Absorption Cross ◽  
High Permeability ◽  
Two Photon Absorption ◽  
Two Photon

DMI could light up the RNA of the nucleus and the cytoplasm in living systems, which not only exhibits larger two-photon absorption cross-sections (981 GM), but also displays high-permeability to plasma membranes of vigorous cells.

Thiophene-based pyridine derivatives: synthesis, crystal structures, two-photon absorption properties and bio-imaging applications in the near-IR region

2016 ◽  
Vol 40 (10) ◽  
pp. 8809-8814 ◽  
Author(s):  
Shasha Xu ◽  
Yingzhong Zhu ◽  
Rui Li ◽  
Jian Su ◽  
Shengli Li ◽  
...  
Keyword(s):  
Cross Sections ◽  
High Stability ◽  
Photon Absorption ◽  
Pyridine Derivatives ◽  
Absorption Properties ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Near Ir ◽  
Bio Imaging ◽  
Low Cytotoxicity

Two novel D–π–A structural chromophores showing large 2PA active cross-sections, low cytotoxicity and high stability in near-IR bio-imaging.

Syntheses and nonlinear absorption properties of conjugated porphyrin supramolecules

2007 ◽  
Vol 11 (05) ◽  
pp. 359-367 ◽  
Author(s):  
Kazuya Ogawa ◽  
Chihiro Hara ◽  
Yoshiaki Kobuke
Keyword(s):  
Cross Section ◽  
Communication System ◽  
Absorption Cross Section ◽  
Enhancement Factor ◽  
Electronic Communication ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Absorption Properties ◽  
Two Photon Absorption ◽  
Two Photon

Self-assemblies consisting of acetylene-linked bisporphyrins with a 4-nitrophenylethynyl substituent and with a phenylethynyl substituent were synthesized. The Q-band of the phenylethynyl-substituted compound appears at 762 nm whereas that of the 4-nitrophenylethynyl-substituted one was red-shifted to 784 nm and intensified. This may be attributed to the participation of the nitro group in the π-electronic communication system. HOMOs and LUMOs were calculated for these compounds using an INDO/S-CI method. The effective two-photon absorption cross-section values of these self-assemblies were measured by using a nanosecond open aperture Z-scan method. The maximum effective two-photon absorption cross-section values of 4-nitrophenylethynyl- and phenylethynyl-substituted bisporphyrins were obtained as 1.2 × 105 GM and 8.1 × 104 GM , respectively, at 890 nm. A 1.5 enhancement factor was obtained by introducing nitro groups, which was similar to the value previously reported for ferrocene- and fullerene-connected supramolecular porphyrin.

scholarly journals Impact of the Subunit Arrangement on the Nonlinear Absorption Properties of Organometallic Complexes with Ruthenium(II) σ-Acetylide and Benzothiadiazole as Building Units §

Inorganics ◽  
2019 ◽  
Vol 7 (5) ◽  
pp. 67
Author(s):  
Eleonora Garoni ◽  
Alessia Colombo ◽  
Kenji Kamada ◽  
Claudia Dragonetti ◽  
Dominique Roberto
Keyword(s):  
Electron Acceptor ◽  
Cross Sections ◽  
Nonlinear Absorption ◽  
Organometallic Complexes ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Absorption Properties ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Resonance Enhancement

In this paper, the nonlinear absorption properties of two complexes consisting of Ru(C≡CPh)(C≡C)(dppe)2 (dppe = Ph2PCH2CH2PPh2) as electron donor (D) and 4,7-di(2-thienyl)benzo[c][1,2,5]thiadiazole as electron acceptor (A) units in two different arrangement, i.e., A–D–A and D–A–D, are presented. They were measured in solution by the femtosecond open-aperture Z-scan method. The complexes show moderate two-photon absorption cross-sections σ(2) of several hundred to one thousand GM (here 1 GM = 10−50 cm4 s molecule−1 photon−1). Although they are formed by the same building units, it was found that the two-photon absorption values of the D–A–D arrangement are six times higher than that of the A–D–A one. This difference can be explained by the number of metal cores (one or two ruthenium centers), the geometrical configurations of the complexes (more or less planar), and the resonance enhancement by lowering the intermediate state.

Synthesis, DNA photocleavage, singlet oxygen photogeneration and two photon absorption properties of ruthenium-phenanthroline porphyrins

2015 ◽  
Vol 19 (09) ◽  
pp. 1046-1052 ◽  
Author(s):  
Ze-Bin Xu ◽  
Fa-Quan Yu ◽  
Fengshou Wu ◽  
Heng Zhang ◽  
Kai Wang ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Cross Section ◽  
Therapeutic Agents ◽  
Photon Absorption ◽  
Quantum Yields ◽  
Absorption Properties ◽  
Dna Photocleavage ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Photochemical Properties

Through a new synthetic route, three ruthenium-phenanthroline porphyrins (RPP1, RPP2 and RPP3) were prepared. Their photophysical and photochemical properties, such as DNA photocleavage activity, singlet-oxygen photogeneration and two-photon absorption (2PA) were evaluated. These porphyrins 1–3 had substantial photocleavage activities, with 71%, 74% and 38% observed at 20 μM. The porphyrins with different substituents on phenathroline group had similar singlet oxygen quantum yields, with ΦΔ values at 0.52, 0.47 and 0.41, respectively. The 2PA cross-section (σ(2)) values of RPP 1–3, measured by the Z-scan method, were calculated to be 152, 172 and 135 GM, respectively, which were around 5-fold higher than that of H2TPP . Thus, these porphyrins, with their good photocleavage activities, 1 O 2 quantum yields and high 2PA cross section, suggest great potential as photodynamic therapeutic agents.

Water-Soluble Paracyclophane Fluorophores with Large Two-Photon Action Cross Sections

2005 ◽  
Vol 871 ◽  
Author(s):  
Han Young Woo ◽  
Dmitry Korystov ◽  
Alexander Mikhailovsky ◽  
Guillermo C. Bazan
Keyword(s):  
Cross Section ◽  
Cross Sections ◽  
Solvent Polarity ◽  
Water Soluble ◽  
Photon Absorption ◽  
Significant Drop ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Donor Ability ◽  
Fine Tune

AbstractA series of tetradonor substituted [2.2]paracyclophane-based two-photon absorption (TPA) fluorophores were designed, synthesized and characterized. Different substituents were chosen to modulate the conjugation and the donor strength and to allow the molecules to be neutral (N series, organic-soluble) or charged (C series, water-soluble). The overall set of compounds series allows us to examine the correlation among the solvent polarity, donor ability of the substituents, and TPA action cross section (ηδd, where δ is the TPA cross section and η is the quantum yield). In water, a significant drop of both δ and η is observed, approximately one-third relative to those in toluene. Weaker donors and/or weaker acceptors with enhanced conjugation are a better choice due to a minimized quenching related to strong charge transfer (CT) upon excitation. One thus needs to fine-tune the magnitude of CT and find an optimal balance among CT,δ and η.

SUBSTITUENT EFFECT ON TWO-PHOTON ABSORPTION PROPERTIES OF FLUORENE DERIVATIVES

2004 ◽  
Vol 13 (03n04) ◽  
pp. 475-479 ◽  
Author(s):  
JUN KAWAMATA ◽  
MASAHARU AKIBA ◽  
YOSHIO INAGAKI ◽  
TAKEHARU TANI ◽  
AKINORI HARADA
Keyword(s):  
Cross Sections ◽  
Substituent Effect ◽  
Femtosecond Pulse ◽  
Substituent Effects ◽  
Photon Absorption ◽  
Absorption Properties ◽  
Two Photon Absorption ◽  
Ti:Sapphire Laser ◽  
Two Photon ◽  
The Relationship

Two novel fluorene derivatives having cationic substituents were synthesized. Two-photon absorption (TPA) properties of the derivatives were evaluated using the fluorescence-based technique with a femtosecond pulse emitted from a Ti:sapphire laser. Maximum TPA cross-sections of the compounds were estimated from the TPA spectra. Based on the results, the relationship between the TPA cross-sections and the substituent effects of the derivatives were discussed.

Tetraphenylethene end-capped [1,2,5]thiadiazolo[3,4-c]pyridine with aggregation-induced emission and large two-photon absorption cross-sections

RSC Advances ◽  
2015 ◽  
Vol 5 (2) ◽  
pp. 1500-1506 ◽  
Author(s):  
Tao Jiang ◽  
Yi Qu ◽  
Bo Li ◽  
Yuting Gao ◽  
Jianli Hua
Keyword(s):  
Cross Sections ◽  
Cell Imaging ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Aggregation Induced Emission ◽  
Two Photon Absorption ◽  
Two Photon ◽  
A Cell

New two-photon absorption dyes (TPEPT1 and TPEPT2) were designed and synthesized. These materials show different 2PA properties and unique AIE effects, in which TPEPT1 with higher brightness was used to perform a cell-imaging proposal.

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