A systematic study of the structure–property relationship of a series of nonlinear optical (NLO) julolidinyl-based chromophores with a thieno[3,2-b]thiophene moiety

Zhang, Airui; Xiao, Hongyan; Cong, Shengyu; Zhang, Maolin; Zhang, Hua; Bo, Shuhui; Wang, Qi; Zhen, Zhen; Liu, Xinhou

doi:10.1039/c4tc01896f

Cited by 41 publications

(12 citation statements)

References 58 publications

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“…26 As a reference reported earlier, β has been calculated at the 6-31+G* level under vacuum 28 . 26 As a reference reported earlier, β has been calculated at the 6-31+G* level under vacuum 28 .…”

Section: Figmentioning

confidence: 86%

Synthesis of novel nonlinear optical chromophores: achieving excellent electro-optic activity by introducing benzene derivative isolation groups into the bridge

Liu

Zhang

et al. 2015

J. Mater. Chem. C

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Three novel second order nonlinear optical (NLO) chromophores based on julolidinyl donors and tricyanofuran (TCF) acceptors linked together via modified polyene π-conjugation with rigid benzene derivative steric hindrance groups (chromophores CL1 and CL2) or unmodified polyene π-conjugation (chromophores CL) moieties as the bridges have been synthesized in good overall yields and systematically characterized. Density functional theory (DFT) was used to calculate the HOMO-LUMO energy gaps and first-order hyperpolarizability (β) of these chromophores. Besides, to determine the redox properties of these chromophores, cyclic voltammetry (CV) experiments were performed. Comparied with CL, after introducting benzene derivative steric hindrance groups into the bridge, chromophores CL1 and CL2 had good thermal stabilities with high thermal decomposition temperatures which were 32°C, 24°C higher than chromophore CL, respectively. Most importantly, the introduction of rigid steric hindrance groups can effectively reduce dipole-dipole interactions to translate their relatively small β values into bulk high EO activities. By doping chromophores CL, CL1 and CL2 with a high loading of 45 wt % in APC, EO coefficients (r33) of up to 121, 197 and 202 pm V -1 at 1310 nm can be achieved, respectively. The r33 values of new chromophores CL1 and CL2 were about 1.6 times of chromophore CL. The high r33 value, good thermal stability and high yield suggest the potential use of the new chromophores in nonlinear optical area.

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Section: Figmentioning

confidence: 86%

Synthesis of novel nonlinear optical chromophores: achieving excellent electro-optic activity by introducing benzene derivative isolation groups into the bridge

Liu

Zhang

et al. 2015

J. Mater. Chem. C

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“…The solvatochromic behaviour of chromophores is strongly influenced by the strength of the donor and acceptor in combination with the p-bridge [27]. The UVeViseNIR absorption spectra of chromophore 10 and 11 were measured in six solvents with different dielectric constants and the corresponding optical absorption data are presented in Table 2.…”

Section: Julolidinyl Donor Nlo Chromophores Containing Thieno [32-b]mentioning

confidence: 99%

Optimization of polycyclic electron-donors based on julolidinyl structure in push–pull chromophores for second order NLO effects

et al. 2015

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“…Dihydroheteropentalenes are in the class of 10 p-electron aromatic systems that play an important role in current optoelectronics.T hieno [3,2-b]thiophene [1] is the most widely studied member of this family,a si tp rovides ab asis for numerous ladder-type thiophene-based heterocycles. [2] The recente xpansion of interest in this class of molecules has been fueled by research applicationss uch as N-type field-effect transistors, [3] mechanosensitivem embrane probes, [4] nonlinear optical materials, [5] in photovoltaicp olymers, [6] hole-transport materials, polymer solar cells, [7] etc. [8] Consequently,n ovel laddertype heteroacenes, such as dibenzothiopheno [6,5-b:6',5'-f]thieno [3,2-b]thiophene, [9] and dithieno[2,3-d:2',3'-d']-thieno [3,2b:3',2'-b']dipyrrole [10] have been recently prepared.…”

Section: Introductionmentioning

confidence: 99%

Z‐Shaped Pyrrolo[3,2‐b]pyrroles and Their Transformation into π‐Expanded Indolo[3,2‐b]indoles

Stężycki

Grzybowski

Clermont

et al. 2016

Chemistry A European J

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Sterically hindered 1,4-dihydropyrrolo[3,2-b]pyrroles possessing ortho-(arylethynyl)phenyl substituents at positions-2 and -5 were efficiently synthesized through a sila-Sonogashira reaction. These unique Z-shaped dyes showed relatively strong fluorescence in solution. Detailed optimization revealed that, in the presence of InCl3, these alkynes readily undergo an intramolecular double cyclization to give hexacyclic products bearing an indolo[3,2-b]indole skeleton in remarkable yields. Steady-state UV-visible spectroscopy revealed that upon photoexcitation, the prepared Z-shaped alkynes undergo mostly radiative relaxation leading to high fluorescence quantum yields. In the case of 7,14-dihydrobenzo[g]benzo[6,7]indolo[3,2-b]indoles, we believe that the substantial planarization of geometry in the excited state, is the underlying reason for the observed large Stokes shifts. The presence of additional electron-withdrawing groups makes it possible to further alter the photophysical properties. The two-photon absorption cross-section values of both families of dyes were found to be modest and the nature of the excited state responsible for two-photon absorption appeared to be strongly affected by the presence of peripheral groups. Serendipitous synthesis of unusual double-Z-shaped alkyne by Sonogashira and Glaser coupling is also reported.

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A systematic study of the structure–property relationship of a series of nonlinear optical (NLO) julolidinyl-based chromophores with a thieno[3,2-b]thiophene moiety

Abstract: A series of NLO chromophores a–d bearing thieno[3,2-b]thiophene (TT) as the conjugated bridge or the lateral moiety have been synthesized and investigated.

Cited by 41 publications

References 58 publications

Synthesis of novel nonlinear optical chromophores: achieving excellent electro-optic activity by introducing benzene derivative isolation groups into the bridge

Synthesis of novel nonlinear optical chromophores: achieving excellent electro-optic activity by introducing benzene derivative isolation groups into the bridge

Optimization of polycyclic electron-donors based on julolidinyl structure in push–pull chromophores for second order NLO effects

Z‐Shaped Pyrrolo[3,2‐b]pyrroles and Their Transformation into π‐Expanded Indolo[3,2‐b]indoles

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