Polycyclic Aromatic Hydrocarbon Solute Probes: Effect of Solvent Polarity on the Ovalene and Benzo[ghi]perylene Fluorescence Emission Fine Structures

Waris, Riaz; Rembert, Michael A.; Sellers, David M.; Acree, William E.; Street, Kenneth W.; Poole, Colin F.; Shetty, Prabhakara H.; Fetzer, John C.

doi:10.1366/0003702884429805

Cited by 46 publications

(7 citation statements)

References 46 publications

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“…Fluorescent probes have a wide range of applications such as monitoring the degree of polymerization, radiation cure technology, and photocurable coatings . Polycyclic aromatic hydrocarbons (PAHs) have commonly been used as fluorescent probes. − Among PAHs, pyrene has been widely studied as a local polarity probe, ,, rendering pyrene and pyrene-based materials as important molecules in the field of photochemistry and photophysics . Such molecules may act as sensitive fluorescent probes that can undergo changes in their spectral properties, which can include quantum-yield values, fluorescence anisotropy, formation of excimers, vibrational structure of pyrene itself, and any external or internal quenching, leading to better knowledge of the surrounding systems .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Detailed Photophysical Studies of Pyrene-Based Molecules Substituted with Extended Chains

et al. 2009

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Applications of conjugated organic compounds in the field of electronics and optoelectronics and of pyrene derivatives as fluorescent probes are well established. The synthesis of the novel pyrene-based 2,11-di-tert-butyl-6,7,15,16-tetrakis(alkoxy/alkythio)quinoxaline[2',3':9,10]phenanthro[4,5-abc]phenazine, TQPP-[t-Bu](2)-[XR](4) (X = O, S; R = C(n)H(2n+1)), is reported along with an in-depth spectroscopic characterization and evaluation of their photophysical properties. Despite their larger core size, the reported TQPP materials showed similar fluorescence behavior to that of pyrene itself, with no significant shift in their fluorescence peak. The fluorescence spectra showed peaks corresponding to the monomer and to the excimer. Even though these TQPP compounds showed poor solubility in various solvents, their solvatochromism could be investigated in different solvents ranging from polar solvents such as methanol to nonpolar solvents such as cyclohexane; Stokes shifts, fluorescence lifetimes, fluorescence quantum yields, as well as radiative and nonradiative rate constants are determined for four of these TQPP materials in various solvents. Quantum yields were found to be low for these TQPP compounds in solvents such as tetrahydrofuran (THF), whereas they were relatively higher in cyclohexane and dioxane. Monomer to excimer intensity ratio versus gross solvent scale (E(T)30) and orientation polarizabilty (Delta f) were correlated. Although TQPP-[t-Bu](2)-[XR](4) displayed similar fluorescent emission and excitation behavior as that of pyrene, a relatively smaller lifetime was observed for these compounds compared to that of pyrene.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Detailed Photophysical Studies of Pyrene-Based Molecules Substituted with Extended Chains

et al. 2009

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“…A systematic experimental investigation on a series of polycyclic aromatic hydrocarbons (PAHs) [8,9,10,11,12,13,14,15,16,17,18] for a variation in selective vibronic bands with respect to solvent polarity show that the PAHs broadly fall in to three categories. The first category of PAHs include pyrene, benzo[ghi]perylene, etc which exhibit a selective emission intensity enhancement of vibronic band I relative to band III (I/III) in polar solvents.…”

Section: Introductionmentioning

confidence: 99%

1,3,6,8-Tetraethynylpyrene and 1,3,6,8-tetrakis (trimethylsilylethynyl) pyrene: Photophysical properties in homogeneous media

Thirunavukkuarasu¹,

Sankararaman²,

Mishra³

2006

Chemical Physics

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“…The monomer and excimer fluorescence lifetimes, fluorescence quantum yield, and radiative and nonradiative rate constants are reported for the TQPP-[ t- Bu] 2 -[SR] 4 and TQPP-[ t- Bu] 2 -[OR] 4 series in Table . The lifetime decays for the oxygen-based series and those of the sulfur-based series are also, respectively, shown in Figures and ; all compounds showed a biexponential lifetime decay, with one of these decays being attributed to that of the monomer and the other to the excimer . The monomer lifetimes range between 3 and 5 ns, whereas the excimer lifetimes range between 11 and 13 ns.…”

Section: Resultsmentioning

confidence: 94%

Effect of Chain Length on the Photophysical Properties of Pyrene-Based Molecules Substituted with Extended Chains

et al. 2009

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The important role played by organic conjugated compounds in the fields of electronics and optoelectronics has led to a vast field of research concerned with synthesizing various complex structures where pi-pi stacking plays a vital role. Pyrene-based molecules are examples of compounds which allow efficient charge transfer through pi-pi molecular stacking. Photophysical studies of such compounds have shown similar behavior as that of pyrene, even though they bear two additional conjugated rings and four long alkyl chains. Chain length may have played an effective role in influencing the pi-pi molecular stacking of such molecules. In continuation of our earlier work (Moustafa, R. M.; Degheili, J. A.; Patra, D.; Kaafarani, B. R. J. Phys. Chem. A 2008, 113, 1235-1243), we hereby synthesize and investigate the role of the chain lengths on the photophysical aspects of 2,11-di-tert-butyl-6,7,15,16-tetrakis(alkoxy/alkythio)quinoxaline-[2',3':9,10]phenanthro[4,5-abc]phenazine, TQPP-[t-Bu](2)-[XR](4) (X = O, S; R = C(n)H(2n+1)). Various photophysical parameters such as Stokes shift, fluorescence lifetime, fluorescence quantum yield, and radiative and nonradiative rate constants are evaluated for TQPP-[t-Bu](2)-[OR](4) and TQPP-[t-Bu](2)-[SR](4) in tetrahydrofuran. The variation of the Stokes shift, fluorescence quantum yield, and lifetime are also correlated with the number of carbons in the alkyl chain R for TQPP-[t-Bu](2)-[OR](4) and TQPP-[t-Bu](2)-[SR](4).

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Polycyclic Aromatic Hydrocarbon Solute Probes: Effect of Solvent Polarity on the Ovalene and Benzo[ghi]perylene Fluorescence Emission Fine Structures

Cited by 46 publications

References 46 publications

Synthesis and Detailed Photophysical Studies of Pyrene-Based Molecules Substituted with Extended Chains

Synthesis and Detailed Photophysical Studies of Pyrene-Based Molecules Substituted with Extended Chains

1,3,6,8-Tetraethynylpyrene and 1,3,6,8-tetrakis (trimethylsilylethynyl) pyrene: Photophysical properties in homogeneous media

Effect of Chain Length on the Photophysical Properties of Pyrene-Based Molecules Substituted with Extended Chains

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