Soluble meso-tetrakis(arylethynyl)porphyrins — synthesis and optical properties

2014 ◽  
Vol 18 (10n11) ◽  
pp. 998-1013 ◽  
Author(s):  
Agnieszka Nowak-Król ◽  
Łukasz G. Łukasiewicz ◽  
Joy E. Haley ◽  
Mikhail Drobizhev ◽  
Aleksander Rebane ◽  
...  
Keyword(s):  
Optical Properties ◽  
Red Light ◽  
Photon Absorption ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Resonance Enhancement ◽  
Order Of Magnitude ◽  
Homo And Lumo ◽  
The One ◽  
First Time

Trans- A 2 B 2-tetrakis(arylethynyl)porphyrins with suitable solubility in CH 2 Cl 2, CHCl 3, EtOAc , acetone and toluene have been obtained for the first time. Among two possible strategies the one comprising the synthesis of 5,15-dibromo-10,20-bis[(isopropylsilyl)ethynyl]porphyrin proved to be more efficient. The pathway towards densely substituted arylacetylenes has been optimized. The use of previously identified 3,4,5-trialkoxyaryl substituent was crucial for achieving the reasonable solubility. The optical properties of meso-substituted tetrakis(arylethynyl)porphyrins were studied showing that strong polarization imparted by direct conjugation of all four substituents with porphyrin core resulted not only in strong absorption of red light but also in a relatively long triplet lifetime. Meso-tetrakis(arylethynyl)porphyrins have a significantly longer lifetime of T1 state than bis(arylethynyl)porphyrins and in their case all the states are mixtures of transitions between the HOMO-1, HOMO and LUMO, LUMO+1 MOs. We show that the presence of two additional arylethynyl substituents at meso-positions enhance the maximum two-photon absorption cross-section of trans- A 2 B 2-tetrakis(arylethynyl)porphyrins by more than one order of magnitude. Maximum values as high as σ2 = 500 GM at 950 nm result from realization of suitable conditions for effective resonance enhancement along with a lowering of the energy and intensification of the two-photon allowed transitions in the Soret region.

Theoretical studies on the one- and two-photon absorption of tetrabenzoporphyrins and phthalocyanines

2004 ◽  
Vol 82 (1) ◽  
pp. 19-26 ◽  
Author(s):  
Xin Zhou ◽  
Ai-Min Ren ◽  
Ji-Kang Feng ◽  
Xiao-Juan Liu
Keyword(s):  
Dipole Moment ◽  
Cross Sections ◽  
Density Functional ◽  
Transition Dipole Moment ◽  
Photon Absorption ◽  
Transition Dipole ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Order Of Magnitude ◽  
The One

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.

Theoretical Investigation on the One- and Two-photon Absorption Properties of Porphyrin-thiophene Chromophores

2009 ◽  
Vol 27 (7) ◽  
pp. 1269-1279 ◽  
Author(s):  
Wenchao LI ◽  
Jikang FENG ◽  
Aimin REN ◽  
Xiangbiao ZHANG ◽  
Chiachung SUN
Keyword(s):  
Theoretical Investigation ◽  
Photon Absorption ◽  
Absorption Properties ◽  
Two Photon Absorption ◽  
Two Photon ◽  
The One

Third-order nonlinear optical properties and two-photon absorption in branched oligothienylenevinylenes

2002 ◽  
Vol 209 (4-6) ◽  
pp. 461-466 ◽  
Author(s):  
I. Fuks-Janczarek ◽  
J-M. Nunzi ◽  
B. Sahraoui ◽  
I.V. Kityk ◽  
J. Berdowski ◽  
...  
Keyword(s):  
Optical Properties ◽  
Nonlinear Optical ◽  
Nonlinear Optical Properties ◽  
Photon Absorption ◽  
Third Order ◽  
Two Photon Absorption ◽  
Two Photon

Computational design of two-photon active organic molecules for infrared responsive materials

2020 ◽  
Vol 8 (29) ◽  
pp. 9867-9873 ◽  
Author(s):  
Robert Zaleśny ◽  
Md. Mehboob Alam ◽  
Paul N. Day ◽  
Kiet A. Nguyen ◽  
Ruth Pachter ◽  
...  
Keyword(s):  
Optical Properties ◽  
Organic Molecules ◽  
Computational Design ◽  
Photon Absorption ◽  
Organic Cations ◽  
Design Rules ◽  
Responsive Materials ◽  
Two Photon Absorption ◽  
Two Photon

Aiming at proposing design rules, the mechanism of two-photon absorption is analyzed in a series of π-conjugated organic cations and their neutral precursors exhibiting aggregation-enhanced optical properties.

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.

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