Synthesis and characterization of NLO chromophore with benzo [1,2-b:4,5-b′]dithiophene unit as π-electron bridge

Si, Peng; Liu, Jialei; Zhen, Zhen; Liu, Xinhou; Lakshminarayana, G.; Kityk, I.V.

doi:10.1016/j.tetlet.2012.04.109

Cited by 23 publications

(9 citation statements)

References 22 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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“…13,16,17 However, it should be noted that the majority of these works were focused on the conjugated bridge and acceptor structures. [18][19][20][21][22][23][24][25] The electron donors, which are important components of NLO chromophores, have received little attention. Among all the materials studied, the dipolar chromophores bearing N,N-dimethyl aniline as a donating group have been widely studied due to their large molecular nonlinearity with signicantly enhanced thermo-and photostabilities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and optical nonlinear property of Y-type chromophores based on double-donor structures with excellent electro-optic activity

et al. 2014

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“…Many efforts have been made to design and synthesize novel NLO chromophores, seeking to engineer NLO molecules both microscopically (b) and macroscopically (r 33 ). 5,10,13 However, the electron acceptor groups and p-conjuncted bridges are widely studied to optimize the comprehensive properties of chromophores; [14][15][16][17][18][19][20][21] the electron donors have not received much attention, though they are important blocks for the construction of NLO chromophores just as the other two. This paper describes our experimental approach to the design and synthesis of the new NLO chromophore HK (Chart 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a novel second-order nonlinear optical chromophore based on a new julolidine donor

Yang

Liu

Wang

et al. 2014

Phys. Chem. Chem. Phys.

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A new chromophore HK containing the cis,cis-1,7-diethoxy-3-isopropyljulolidine group as a novel electron-donor, thiophene as a π-conjugated bridge and a tricyanofuran (TCF) acceptor has been synthesized and systematically investigated in this paper. Its corresponding chromophore FTC using 4-(diethyl amino)benzyl as the electron donor group was also prepared for comparison. This is the first time that the cis,cis-1,7-diethoxy-3-isopropyljulolidine group was introduced into NLO materials. Density functional theory (DFT) was used to calculate the HOMO-LUMO energy gap and first-order hyperpolarizability (β) of the new chromophore. The HOMO-LUMO gap was also investigated by cyclic voltammetry (CV). Upon using the cis,cis-1,7-diethoxy-3-isopropyljulolidine group as the donor, a reduced energy gap of 1.007 eV was obtained compared with chromophore FTC (ΔE = 1.529 eV). The high molecular hyperpolarizability of the new chromophore can be effectively translated into large electro-optic (EO) coefficients (r33) in poled polymers. The doped films containing the new chromophore HK showed a value of 72 pm V(-1) at the concentration of 25 wt% at 1310 nm. This value is almost two times higher than the EO activity of the usually reported traditional (N,N-diethyl) aniline nonlinear optical (NLO) chromophore FTC. High r33 values indicated that the new julolidine donor can efficiently improve the electron-donating ability and reduce intermolecular electrostatic interactions, thus enhancing the macroscopic EO activity. These properties, together with good solubility, suggest the potential use of the new chromophore in advanced materials devices.

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Synthesis and characterization of NLO chromophore with benzo [1,2-b:4,5-b′]dithiophene unit as π-electron bridge

Cited by 23 publications

References 22 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 optical nonlinear property of Y-type chromophores based on double-donor structures with excellent electro-optic activity

Synthesis and characterization of a novel second-order nonlinear optical chromophore based on a new julolidine donor

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