Alkyl substituent effects on J- or H-aggregate formation of bisazomethine dyes

Kinashi, Kenji; Lee, Kyun Phyo; Matsumoto, Shinya; Ishida, Kenji; Ueda, Y.

doi:10.1016/j.dyepig.2011.05.024

Cited by 26 publications

(13 citation statements)

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“…Some recent works have demonstrated the possibility of synthesizing D-A or D-A-D systems by means of more environmental friendly methods such as click chemistry [5] or basic condensations [6]. Additionally, the two-fold condensation of aromatic aldehydes onto commercial (Z)-2,3-diaminomaleonitrile to form D-A-D compounds with a central diiminofumaronitrile electro-deficient group has been scantly studied and most articles have been focused on the optical [7] or aggregative [8] properties of the compounds. A first report on the use of N,N-bis [4-(N,N-diethylamino)benzylidene]diaminomaleonitrile as active material in a Schottky solar cell has been published some years ago leading to a PCE of 0.38% under low intensity illumination [9].…”

Section: Introductionmentioning

confidence: 99%

One step synthesis of D-A-D chromophores as active materials for organic solar cells by basic condensation

et al. 2015

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Donor-Acceptor-Donor conjugated systems are synthesized in good yield by double condensation of aromatic aldehydes of triarylamines with 2,3-diaminomaleonitrile under microwave activation with trifluoroacetic acid as catalyst. The electronic properties of the compounds are investigated and discussed and a first evaluation of their potential as donor material in organic photovoltaic cells is presented.

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Section: Introductionmentioning

confidence: 99%

One step synthesis of D-A-D chromophores as active materials for organic solar cells by basic condensation

et al. 2015

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“…N,N'-bis [4-(N,N-diethylamino)benzylidene]diaminomaleonitrile (DE2) 25 (Sheme S1, ESI †) formed J-aggregates in thin deposited films and can be further applied to organic solar cells and fieldeffect transistors. [26][27][28][29][30][31][32] Its crystal structure analysis indicated that DE2 undergoes a structural phase transition at a low temperature (LT, 93 K). 33 The volume of the unit cell at LT is twice that of a room temperature (RT, 293 K) phase, and the number of molecules in the unit cell changes from Z = 3 (Z′ = 1.5) to Z = 6 (Z′= 3).…”

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confidence: 99%

Macroscopic crystalline deformation in an organic dye during reversible phase transition caused by alkyl disorder

2018

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“…Following chloroform evaporation, head‐to‐tail stacking of the anthraquinones in the R‐phase produces a J‐aggregate‐type assembly, [ 61,63,64 ] accounting for the red film appearance. Notably, pronounced interdigitation of the diacetylene sidechains (Figure 5A, right) is aided by the apolar solvent, yielding significantly thinner lamellae in the R‐phase compared to the Y‐phase (lamellae width of 2.1 nm in case of the R‐phase compared to 5.4 nm for the Y‐phase, Figure 5A).…”

Section: Resultsmentioning

confidence: 99%

Aggregation‐Dependent Chromism and Photopolymerization of Aminoanthraquinone‐Substituted Diacetylenes

Bisht

Dhyani

Jelinek

2020

Advanced Optical Materials

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Polydiacetylenes have attracted significant interest for their unique chromatic properties and applications in sensing, imaging, and optics. Here, it is demonstrated that aminoanthraquinone‐substituted diacetylenes exhibit distinct aggregation‐dependent chromatic properties, affected by the alignment of both the aminoanthraquinone headgroups and diacetylene sidechains. Specifically, it is shown that aminoanthraquinone‐diacetylene monomers adopt different film organizations depending upon the polarity of the solvent employed for predissolution. In particular, a yellow aminoanthraquinone‐diacetylene phase, which undergoes photopolymerization upon ultraviolet irradiation, is produced upon dissolution in polar organic solvents prior to deposition and drying on solid substrates. In contrast, a red phase that can not be polymerized is observed when the monomers are predissolved in apolar solvents. Microscopic and spectroscopic analyses indicate that the optical properties of the films are determined by the degree of overlap between the aminoanthraquinone headgroups as well as the alignment of the diacetylene sidechains; both factors are intimately affected by interactions of the monomers with solvent molecules. It is shown that the aggregation‐dependent diacetylene films exhibit remarkable solvochromic, thermochromic, and mechanochromic properties. The aminoanthraquinone‐substituted diacetylenes may facilitate chromatic tuning of polydiacetylene systems in the solid state, determined by solvent‐ and intermolecular interactions and concomitant self‐assembly of the pendant sidechains and aromatic headgroups.

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Alkyl substituent effects on J- or H-aggregate formation of bisazomethine dyes

Cited by 26 publications

References 26 publications

One step synthesis of D-A-D chromophores as active materials for organic solar cells by basic condensation

One step synthesis of D-A-D chromophores as active materials for organic solar cells by basic condensation

Macroscopic crystalline deformation in an organic dye during reversible phase transition caused by alkyl disorder

Aggregation‐Dependent Chromism and Photopolymerization of Aminoanthraquinone‐Substituted Diacetylenes

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