Band gap tunable for near-infrared absorbing chromophores with multi-triphenylamine and tris (thieno)hexaazatriphenylenes acceptors

Gao, Baoxiang; Xia, Defang; Geng, Yanhou; Cheng, Yanxiang; Wang, Lixiang

doi:10.1016/j.tetlet.2010.02.039

Cited by 11 publications

(4 citation statements)

References 31 publications

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“…Compound 2,5-bis(4-(diphenylamino)phenyl)thiophene-3,4-diamine was synthesized according to previously reported literature . Compound DTPD was synthesized similarly as described for synthesis of 1,4-dibromophenazine, black solid, 35% yield (50 mg): 1 H NMR (400 MHz, CD 2 Cl 2 , δ ppm) 8.21–8.19 (m, 4H), 7.82–7.80 (m, 2H), 7.50–7.48 (m, 2H), 7.23 (t, 8H, J = 7.6 Hz), 7.10–7.09 (m, 12H), 7.00 (t, 4H, J = 7.2 Hz); 13 C NMR (100 MHz, CD 2 Cl 2 , δ ppm) 147.5, 143.9, 130.7, 130.6, 129.6, 128.6, 125.0, 123.6, 123.4; MALDI-TOF m / z 672, calcd 672.2; HRMS (ESI, m / z ) [(M + H) + ] calcd for C 46 H 33 N 4 S 673.2426, found 673.2422.…”

Section: Methodsmentioning

confidence: 99%

Controlling the Charge Transfer in D–A–D Chromophores Based on Pyrazine Derivatives

Fan

et al. 2014

J. Org. Chem.

110

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A series of symmetrical donor-acceptor-donor (D-A-D) chromophores bearing various electron-withdrawing groups, such as quinoxaline (Qx), benzo[g]quinoxaline (BQ), phenazine (Pz), benzo[b]phenazine (BP), thieno[3,4-b]pyrazine (TP), and thieno[3,4-b]quinoxaline (TQ), has been designed and synthesized. Intramolecular charge transfer (ICT) interactions can be found for all the chromophores due to the electron-withdrawing properties of the two imine nitrogens in the pyrazine ring and the electron-donating properties of the other two amine nitrogens in the two triphenylamines. Upon the fusion of either benzene or thiophene ring on the pyrazine acceptor unit, the ICT interactions are strengthened, which results in the bathochromically shifted ICT band. Moreover, the thiophene ring is superior to the benzene ring in enlarging the ICT interaction and expanding the absorption spectrum. Typically, when a thiophene ring is fused on the Qx unit in DQxD, a near-infrared dye is realized in simple chromophore DTQD, which displays the maximum absorption wavelength at 716 nm with the threshold over 900 nm. This is probably due to the enhanced charge density on the acceptor moiety and better orbital overlap, as revealed by theoretical calculation. These results suggest that extending the conjugation of a pyrazine acceptor in an orthogonal direction to the D-A-D backbone can dramatically improve the ICT interactions.

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Section: Methodsmentioning

confidence: 99%

Controlling the Charge Transfer in D–A–D Chromophores Based on Pyrazine Derivatives

Fan

et al. 2014

J. Org. Chem.

110

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“…Organic donor–acceptor (D–A) compounds have potential in various fields including nonlinear optics, − organic light-emitting diodes, − and organic photovoltaics. − In particular, small molecule D–A motifs are comparatively easy to purify and have a well-defined structure, relative to their polymer counterparts. , The optical behavior of D–A dyes is typically associated with a photoinduced charge transfer (CT). This occurs on the absorption of a photon, which results in the donation of electron density from an electron-rich (donor) group to an electron-withdrawing (acceptor) group. − By altering the coupling of the D–A interaction through electronic and geometric factors, control over the photophysical properties is achieved. , CT processes result in the formation of “zwitterionic” excited states.…”

Section: Introductionmentioning

confidence: 99%

When “Donor–Acceptor” Dyes Delocalize: A Spectroscopic and Computational Study of D–A Dyes Using “Michler’s Base”

et al. 2019

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In this study, we show that the “Michler’s base” motif can be combined in a donor–acceptor arrangement with a range of acceptor units (indandione, indandione with cyano substituents, barbituric acid, or rhodanine) to give photophysical properties that are dominated by delocalized excited states. By changing the acceptor unit and by altering the planarity of this system, it is possible to tune the low-energy absorption feature in terms of intensity from 23 000 to 67 000 M–1 cm–1 and energy between 500 and 700 nm. Resonance Raman spectroscopy and time-dependent density functional theory indicate that this absorption feature has two underlying transitions: a weaker charge-transfer transition around 500 nm and a strong mixed or delocalized transition between 550 and 700 nm. Generally, these compounds are not strongly emissive; however, dual emission is observed, and the relative intensity of the two states can be modulated by solvent polarity. The energy of these emissive states does not correlate with the Lippert–Mataga analysis in which the Stokes shift is related to the solvent polarity (Δf).

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“…On the other hand, C 3 symmetric octupolar molecules have found application in nonlinear optics . In this regard, the HAT core with branched arms (usually six) plays an important role. − …”

Section: Introductionmentioning

confidence: 99%

Extending Hexaazatriphenylene with Mono-/Bithiophenes in Acceptor–Donor Diads and Acceptor–Donor–Acceptor Triads

et al. 2016

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Three new hexaazatriphenylene (HAT)-based electron-accepting molecules with octupolar disc-like symmetry that combine the HAT core with six branches of electron-donor thiophenes in two modalities have been synthesized: (i) with six donor thiophenes and bithiophenes delineating a six-donor-toone-acceptor (6−1) profile and (ii) with six donor−acceptor branches configuring a 6−6−1 acceptor−donor−acceptor triad. The 6-fold accumulation of donors and acceptors in the periphery of the HAT core is expected to tune the molecular electronic and optical properties. An exhaustive analysis of these properties as a function of the 6−1 and 6−6−1 stoichiometry of the molecules is described by combining a palette of experimental spectroscopic techniques such as electronic absorption (from the ground electronic and excited states), emission (fluorescence and phosphorescence), ultraviolet photoelectron spectroscopy, spectroelectrochemistry, and vibrational Raman have been implemented, all combined with electrochemistry and molecular theoretical modeling. A particular focus on the charged species and the charge distribution around the 6−1 and 6−6−1 patterns is conducted. Structure−property relationships have been outlined. The complete understanding of all these properties might help to design improved chromophores based on the HAT structure and to anticipate new properties.

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Band gap tunable for near-infrared absorbing chromophores with multi-triphenylamine and tris (thieno)hexaazatriphenylenes acceptors

Cited by 11 publications

References 31 publications

Controlling the Charge Transfer in D–A–D Chromophores Based on Pyrazine Derivatives

Controlling the Charge Transfer in D–A–D Chromophores Based on Pyrazine Derivatives

When “Donor–Acceptor” Dyes Delocalize: A Spectroscopic and Computational Study of D–A Dyes Using “Michler’s Base”

Extending Hexaazatriphenylene with Mono-/Bithiophenes in Acceptor–Donor Diads and Acceptor–Donor–Acceptor Triads

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