Synthesis, crystal structure, and spectroscopic properties of new stilbazolium salt with enlarged π-conjugated system

Todorova, Mina; Bakalska, Rumyana; Kolev, Tsonko

doi:10.1016/j.saa.2013.01.088

Cited by 15 publications

(4 citation statements)

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“…In stilbazolium dyes the positive charge of the chromophore is localized on the pyridinium moiety, but it shifts upon photoexcitation toward the amino moiety, giving rise to the different forms of the chromophore, that is, ionic in the ground state and quinoid in the excited state, from which photoluminescence occurs (Figure b). This results in one of the largest Stokes shifts, up to ∼7000 cm –1 (∼0.87 eV), reported by Todorova et al In addition, solvents of different polarity interact differently with the two forms, making it possible that either ionic or quinoid forms are present in various solvents. Todorova and coauthors showed that Stokes shift increases from stilbazolium dyes with pyridinium and benzene nuclei (mononuclear) to quinolinium and benzene nuclei (one and half nuclear), and finally to those possessing quinolinium and naphthalene nuclei (binuclear) in almost all solvents compared.…”

Section: Conversion and Decay Of Excitonsmentioning

confidence: 97%

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Dynamics of Excitons in Conjugated Molecules and Organic Semiconductor Systems

Dimitriev

2022

Chem. Rev.

109

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The exciton, an excited electron–hole pair bound by Coulomb attraction, plays a key role in photophysics of organic molecules and drives practically important phenomena such as photoinduced mechanical motions of a molecule, photochemical conversions, energy transfer, generation of free charge carriers, etc. Its behavior in extended π-conjugated molecules and disordered organic films is very different and very rich compared with exciton behavior in inorganic semiconductor crystals. Due to the high degree of variability of organic systems themselves, the exciton not only exerts changes on molecules that carry it but undergoes its own changes during all phases of its lifetime, that is, birth, conversion and transport, and decay. The goal of this review is to give a systematic and comprehensive view on exciton behavior in π-conjugated molecules and molecular assemblies at all phases of exciton evolution with emphasis on rates typical for this dynamic picture and various consequences of the above dynamics. To uncover the rich variety of exciton behavior, details of exciton formation, exciton transport, exciton energy conversion, direct and reverse intersystem crossing, and radiative and nonradiative decay are considered in different systems, where these processes lead to or are influenced by static and dynamic disorder, charge distribution symmetry breaking, photoinduced reactions, electron and proton transfer, structural rearrangements, exciton coupling with vibrations and intermediate particles, and exciton dissociation and annihilation as well.

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Section: Conversion and Decay Of Excitonsmentioning

confidence: 97%

“…Copyright 2019 American Chemical Society. (b) Ground state ionic and excited quinoid forms of stilbazolium dye according to Todorova et al and corresponding ground-state absorption (black) and excited-state emission (red, λ exc = 405 nm) spectra.…”

Section: Conversion and Decay Of Excitonsmentioning

confidence: 99%

Dynamics of Excitons in Conjugated Molecules and Organic Semiconductor Systems

Dimitriev

2022

Chem. Rev.

109

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“…14). Information about the crystalline structure of some recently developed cyanine dyes such as stilbazoliums (5) [62] or substituted squaraines (6) [63] may also be found in the literature.…”

Section: Crystalline-state Dyes and Pigmentsmentioning

confidence: 99%

WITHDRAWN: Hydrogen-bonding versus π–π stacking in the design of organic semiconductors: From dyes to oligomers

Gospodinova¹,

Tomšík²

2014

Progress in Polymer Science

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This review discusses some general aspects of the highly directional intermolecular interactions in organic solids, followed by an overview of π-conjugated systems exhibiting directional preference in the intermolecular connection and demonstrating enhanced energy and/or charge carrier transfer. As examples, "small" dyes and pigments, "intermediate-sized" N-heteroacenes, and "large" hydrogen-bonded oligomers are considered. In all of these systems the intermolecular interactions between polarized peripheries of the π-conjugated moieties ensure a preferential direction in the molecular packing. The most important among these interactions are hydrogen bonds (both strong and weak). As demonstrated recently, hydrogen bonding represents a dominant attractive force even for molecules with different polarization of the π-conjugated aromatic or heterocyclic moieties, considered to be the most favorable condition for "face-to-face" orientation (π−π stacking).The solid-state anisotropy, most likely, results from the nematic liquid-crystalline ordering of both thermotropic and lyotropic origin. Moreover, the unique efficiency of the exciton diffusion in the J-aggregates of dyes indicates significant potential of the nematic liquidcrystalline state itself for the design of organic semiconductors.

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“…The bands located at $1167 cm À1 and $1180 cm À1 are attributed to deformation vibration of the -CH 3 of the Ndimethylamino group. 50 The band at $984 cm À1 can be assigned to a mode consisting of the in-phase ethylenic CH wag. 51 The out-of-plane CH bending vibration is seen at $810 cm À1 as weak signals.…”

Section: Resultsmentioning

confidence: 99%