Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides

Chen, Kew‐Yu; Fang, Tzu-Chien; Chang, Min

doi:10.1016/j.dyepig.2011.06.023

Cited by 37 publications

(32 citation statements)

References 36 publications

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“…Larger effects are found for the strongly donating planar NH 2 that induces a significant bathochromic shift to 2.81 eV and reduces the oscillator strength to 0.25 (from 0.48); the calculated transition energy is slightly higher than the experimental value of 2.57 eV measured in CHCl 3 . Interestingly, while the amino substituent is planar in NDI, it adopts a pyramidal conformation in PDI which, in the latter case, induces a significantly smaller redshift of the S 0 –S 1 transition from 2.36 to 2.15 eV . The heavier group‐15 substituents also favor pyramidalized conformations in NDI with S 0 –S 1 transition energies of 3.04, 3.15, and 2.95 eV for PH 2 , AsH 2 , and SbH 2, respectively, and decreasing oscillator strengths down the group.…”

Section: Resultsmentioning

confidence: 68%

Substituent effects on the optical properties of naphthalenediimides: A frontier orbital analysis across the periodic table

Mulder

Guerra²,

Slootweg

et al. 2015

J Comput Chem

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A comprehensive theoretical treatment is presented for the electronic excitation spectra of ca. 50 different mono-, di-, and tetrasubstituted naphthalenediimides (NDI) using time-dependent density functional theory (TDDFT) at ZORA-CAM-B3LYP/TZ2P//ZORA-BP86/TZ2P with COSMO for simulating the effect of dichloromethane (DCM) solution. The substituents -XHn are from groups 14-17 and rows 2-5 of the periodic table. The lowest dipole-allowed singlet excitation (S0 -S1 ) of the monosubstituted NDIs can be tuned from 3.39 eV for -F to 2.42 eV for -TeH, while the S0 -S2 transition is less sensitive to substitution with energies ranging between 3.67 eV for -CH3 and 3.44 eV for -SbH2 . In the case of NDIs with group-15 and -16 substituents, the optical transitions strongly depend on the extent to which -XHn is planar or pyramidal as well as on the possible formation of intramolecular hydrogen bonds. The accumulative effect of double and quadruple substitution leads in general to increasing bathochromic shifts, but the increased steric hindrance in tetrasubstituted NDIs can lead to deformations that diminish the effectiveness of the substituents. Detailed analyses of the Kohn-Sham orbital electronic structure in monosubstituted NDIs reveal the mesomeric destabilization of the HOMO as the primary cause of the bathochromic shift of the S0-S1 transition.

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Section: Resultsmentioning

confidence: 68%

Substituent effects on the optical properties of naphthalenediimides: A frontier orbital analysis across the periodic table

Mulder

Guerra²,

Slootweg

et al. 2015

J Comput Chem

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“…Rubrene (Alfa Aesar, 97%) was used as purchased. PDIB, PDIB-2OPh and PDIB-4OPh were synthesized according to procedures described in the literature 29,30,31 . All crystals were grown using the physical vapor transport (PVT) technique 32 under a stream of ultrapure Ar gas.…”

Section: Experimental Methodsmentioning

confidence: 99%

Effect of Molecular Stacking on Exciton Diffusion in Crystalline Organic Semiconductors

et al. 2015

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Exciton diffusion is at the heart of most organic optoelectronic devices' operation, and it is currently the most limiting factor to their achieving high efficiency. It is deeply related to molecular organization, as it depends on intermolecular distances and orbital overlap. However, there is no clear guideline for how to improve exciton diffusion with regard to molecular design and structure. Here, we use single-crystal charge-transfer interfaces to probe favorable exciton diffusion. Photoresponse measurements on interfaces between perylenediimides and rubrene show a higher photocurrent yield (+50%) and extended spectral coverage (+100 nm) when there is increased dimensionality of the percolation network and stronger orbital overlap. This is achieved by very short interstack distances in different directional axes, which favors exciton diffusion by a Dexter mechanism. Even if the core of the molecule shows strong deviation from planarity, the similar electrical resistance of the different systems, planar and nonplanar, shows that electronic transport is not compromised. These results highlight the impact of molecular organization in device performance and the necessity of optimizing it to take full advantage of the materials' properties.

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“…Calculations of electronic absorption spectra were done with the TD‐DFT method at the B3LYP/6‐31G(d) level on the basis of the optimized ground‐state structures. As this method has been widely used and given reliable results in the past reports . The results were given in Table .…”

Section: Discussionmentioning

confidence: 97%

The Photostability of Two Optical Materials Based on Perylene Diimide Substituted by Different Aromatic Groups at the Bay Area

Zeng

2017

Journal of Heterocyclic Chem

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The perylene diimide substituented by thiophene rings at bay area shows photoactivity and can be used as a photo sensor, but another one substituented by mestylene groups is photostable. The single crystal of 1,7‐mesitylene perylene diimide was obtained. X‐ray diffraction data of the crystal revealed that the plane of the perylene core was hardly twisted by introduction of mesitylene groups. These mestylene groups are like clips maintaining the planarity of the perylene core. Density functional theory calculation was applied to study the difference of photophysical and photochemical properties. The discovery is valuable for design guidance of perylene diimides.

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Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides

Cited by 37 publications

References 36 publications

Substituent effects on the optical properties of naphthalenediimides: A frontier orbital analysis across the periodic table

Substituent effects on the optical properties of naphthalenediimides: A frontier orbital analysis across the periodic table

Effect of Molecular Stacking on Exciton Diffusion in Crystalline Organic Semiconductors

The Photostability of Two Optical Materials Based on Perylene Diimide Substituted by Different Aromatic Groups at the Bay Area

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