Ideal polymethine state of merocyanines in the crystal

Shishkina, Svitlana V.; Dyakonenko, Viktoriya V.; Ishchenko, A. A.; Kulinich, A. V.

doi:10.1007/s11224-021-01834-7

Cited by 5 publications

(5 citation statements)

References 62 publications

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“…Small bond lengths alternations are typical for dicyanomethylene‐type merocyanines. [22a] However, in contrast to typical stacking, for merocyanine 6 h weak intermolecular hydrogen bonds between the amino groups and the cyano groups form infinite zig‐zag chains in the crystal lattice (Figure 2 ).…”

Section: Resultsmentioning

confidence: 97%

Cyclohexene‐Embedded Dicyanomethylene Merocyanines – Consecutive Three‐Component Coupling‐Addition Synthesis and Chromophore Characteristics

Papadopoulos,

Reiss,

Mayer

et al. 2023

ChemistryOpen

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A concise and efficient consecutive three‐component alkynylation‐addition synthesis of cyclohexene‐embedded dicyanomethylene merocyanines furnishes a small library of dyes in moderate to excellent yield. The dyes possess strong absorption coefficients of the longest wavelength absorption bands. According to the crystal structure, the small bond length alternations account for a highly delocalized electronic ground state. The electronic structure of the absorption bands is qualitatively rationalized by TDDFT calculations, which explain that intense HOMO‐LUMO transitions along the merocyanine axis lead to cyanine similar Stokes shifts.

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Section: Resultsmentioning

confidence: 97%

Cyclohexene‐Embedded Dicyanomethylene Merocyanines – Consecutive Three‐Component Coupling‐Addition Synthesis and Chromophore Characteristics

Papadopoulos,

Reiss,

Mayer

et al. 2023

ChemistryOpen

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“…The general patterns of the merocyanine structure in the solid state were first traced using a set of dyes 6-11 and 92-94 [112] of the same structural type but of different dipolarity. [113][114][115] Among them, indole derivatives 6-8 exhibit pronounced positive solvatochromism, benzothiazole derivatives 9-11 have inverse solvatochromism with a prevalence of positive, and benzimidazole-based dyes 92-94 show negative solvatochromism when going from chloroform to more polar solvents. The choice of malononitrile as the acceptor endgroup was due to the lower tendency of its derivatives to embed polar solvent molecules in the crystal lattice compared to merocyanines containing carbonyl groups in the electronacceptor moiety.…”

Section: Structure Of Merocyanines In the Crystal Statementioning

confidence: 99%

“…The general patterns of the merocyanine structure in the solid state were first traced using a set of dyes 6 – 11 and 92 – 94 [112] of the same structural type but of different dipolarity [113–115] . Among them, indole derivatives 6 – 8 exhibit pronounced positive solvatochromism, benzothiazole derivatives 9 – 11 have inverse solvatochromism with a prevalence of positive, and benzimidazole‐based dyes 92 – 94 show negative solvatochromism when going from chloroform to more polar solvents.…”

Section: Electronic Structure and Spectral Properties Of Merocyanine ...mentioning

confidence: 99%

Design and Photonics of Merocyanine Dyes

Kulinich,

Ishchenko

2023

The Chemical Record

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Merocyanines, thanks to their easily adjustable electronic structure, appear to be the most versatile and promising functional dyes. Their D–π–A framework offers ample opportunities for custom design through variations in both donor/acceptor end‐groups and the π‐conjugated polymethine chain, and leads to a broad range of practical properties, including noticeable solvatochromism, high polarizability/hyperpolarizabilities, and the ability to sensitize various physicochemical processes. Accordingly, merocyanines are applied and extensively studied in various fields, such as light‐converting materials for optoelectronics, nonlinear optics, optical storage, solar cells, fluorescent probes, and antitumor agents in photodynamic therapy. This review encompasses both classical and novel more important publications on the structure–property relationships in merocyanines, with particular emphasis on the results by A. I. Kiprianov and his followers in Institute of Organic Chemistry in Kyiv, Ukraine.

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“…So far, this aspect has only been investigated to a limited extent, although the structure formation of MCs has been well studied for single crystals and spin coated films of several nm thickness. 5,6,12 Only few growth studies on self-assembled MC monolayers at substrate interfaces have been published, [13][14][15] possibly, because MCs are rather complex molecules, compared to other standard organic semiconductor molecules, for which the adsorption on surfaces has been thoroughly investigated. [16][17][18][19] In particular, MCs are non-planar, of low symmetry, and exhibit non-rigid sidegroups with structural freedom.…”

Section: Introductionmentioning

confidence: 99%