Novel electro-optic chromophores based on substituted benzo[1,2-b:4,5-b′]dithiophene π-conjugated bridges

Si, Peng; Liu, Jialei; Deng, Guowei; Huang, Heyan; Xu, Huajun; Bo, Shuhui; Qiu, Ling; Zhen, Zhen; Liu, Xinhou

doi:10.1039/c4ra01767f

Cited by 19 publications

(9 citation statements)

References 45 publications

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“…Benzodithiophene (BDT) derivatives 4 and 5 could be obtained in good yields by double formylation in the α position of the thiophene rings following methods reported in the literature. The chemical shift of the key aromatic protons in the β‐position of the thiophene rings, are identical to those reported in the literature for a longer unbranched alkyl chain derivative ( n ‐dodecyl substituted diformyl BDT, analogous to 4 ) and a branched alkyl chain derivative (2‐ehtylhexyl substituted diformyl BDT, analogous to 5 ) . This data confirms the accessibility of the π‐surfaces and the absence of self‐aggregation and π–π stacking independently by the steric hindrance of the O‐alkyl substituents.…”

Section: Resultssupporting

confidence: 86%

Donor–acceptor conjugated copolymers incorporating tetrafluorobenzene as the π‐electron deficient unit

Nitti

Debattista

Abbondanza³

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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We present the synthesis and characterization of a new family of perfectly alternating conjugated polymers, obtained through different methodologies (Stille, Direct Arylation, and Horner–Wadsworth–Emmons polymerizations). The polymers comprise either 2,5‐dialkoxybenzene or benzodithiophene electron rich units, and 1,2,4,5‐tetrafluorobenzene as the electron‐deficient unit, eventually separated by a vinylene bridge, if suitable monomers and HWE polymerization procedures are used. As shown by NMR spectroscopy, the introduction of the fluorinated aromatic units brings complications in the polymer stereodefinition in the HWE polymerization, and regiodefinition in the case of the Direct Arylation. The polymers show moderate degrees of polymerization (up to 10 repeating alternating units in the backbone), which are however significant enough to unravel interesting properties such as energy HOMO–LUMO gaps and aggregation behavior in solution at room temperature. In depth calculations fully confirmed the aggregation tendency, highlighting the key role of the benzodithiophene as the donor component when in combination with the tetrafluorobenzene unit. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 1601–1610

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Section: Resultssupporting

confidence: 86%

Donor–acceptor conjugated copolymers incorporating tetrafluorobenzene as the π‐electron deficient unit

Nitti

Debattista

Abbondanza³

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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“…Wittig reaction using the ylide derivative of julolidine 349 has also been reported (Scheme ) . Reduction of 360 with NaBH 4 followed by reaction with triphenylphosphonium bromide generated the ylide 361 , which was directly subjected to reaction with 362 to afford 363 in 54 % yield (mixture of diastereoisomers at Z:E 82:18).…”

Section: Reactions From Julolidinesmentioning

confidence: 99%

“…Finally, the condensation reaction of 363 with TCF led to formation of 364 with 48 % yield at the Z:E proportion of 55:45. Compound 364 showed an EO coefficient of 102 pm V –1 in 30 wt.‐% APC film at 1310 nm …”

Section: Reactions From Julolidinesmentioning

confidence: 99%

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Varejão

Fernandes

2019

Eur J Org Chem

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Julolidines constitute a class of N‐heterocycle compounds which have in common the 2,3,6,7‐tetrahydro‐1H,5H‐benzo[1,2]quinolizine ring. Due mainly to its fluorescence properties, such structures have shown potential application in a range of scientific and technological areas and have attracted attention of a great variety of research groups. For example, julolidines have been used for detection of ions and volatile compounds in environmental and biological samples, to the construction of dye‐sensitized solar cells, photoconductive materials and as fluorescent sensors for bioimaging. This review summarizes the strategies reported to the synthesis of the julolidine ring and the principal modifications for obtaining more complex julolidine derivatives with improved fluorescence properties of these compounds. In this context, aldol condensation, olefination, imine synthesis, and cross‐coupling reactions have been extensively explored and discussed. Examples of applications, which illustrate the great potential of such structures, will also be briefly presented.

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“…Organic chromophores with donor and acceptor substitution are widely used for the construction of donor−acceptor (D‐A) molecular systems,, due to their potential applications in organic light emitting diodes (OLEDs), nonlinear optics (NLO), and organic photovoltaics…”

Section: Introductionmentioning

confidence: 99%

Triphenylamine Functionalized Unsymmetrical Quinoxalines

Bijesh

Misra

2018

Asian J Org Chem

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A family of unsymmetrical quinoxalines 11-18 of types D-A-π-D and D-A-A'-D' have been designed and synthesized by the Suzuki, Heck, Sonogashira, Ullmann coupling and [2 + 2] cycloadditionÀ retroelectrocyclic ring opening reactions. A systematic study was performed to explore the effect of donor, acceptor and π-linker on the triphenylamine functionalized quinoxalines. The electronic absorption spectra of the ethynyl bridged quinoxaline 14 show red shifted absorption in the high-energy region compared to quinoxaline 13. The quinoxalines 17 and 18 exhibit red shifted absorption in the near-infrared (NIR) region due to the incorporation of strong TCNE/TCNQ acceptor units. The TGA data reveals that triphenylethylene substituted quinoxaline 15 shows higher thermal stability compared to other quinoxalines. The electrochemical data exhibit strong electronic communication in quinoxalines 11-18. The incorporation of TCNE/TCNQ acceptor units results in greater stabilization of LUMO levels and low HOMOÀ LUMO energy gap in 17 and 18 which was supported by computational studies.

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Novel electro-optic chromophores based on substituted benzo[1,2-b:4,5-b′]dithiophene π-conjugated bridges

Abstract: The electro-optic coefficient of benzo[1,2-b:4,5-b′]dithiophene unit (BDT)-based chromophores was improved to 102 pm V−1 with suitable isolation groups and electron donors.

Cited by 19 publications

References 45 publications

Donor–acceptor conjugated copolymers incorporating tetrafluorobenzene as the π‐electron deficient unit

Donor–acceptor conjugated copolymers incorporating tetrafluorobenzene as the π‐electron deficient unit

Synthesis and Derivatization of Julolidine: A Powerful Heterocyclic Structure

Triphenylamine Functionalized Unsymmetrical Quinoxalines

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