Synthesis, photophysical, structural and electronic properties of novel regioisomerically pure 1,7-disubstituted perylene-3,4,9,10-tetracarboxylic monoimide dibutylester derivatives

Ozser, Mustafa E.; Mohiuddin, Obaidullah

doi:10.1016/j.molstruc.2018.01.023

Cited by 7 publications

(5 citation statements)

References 27 publications

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“…The spectrum of 9 demonstrates features at 1720 and 1706 cm −1 that are characteristic of ester carbonyls. 55 The spectrum of 10 demonstrates peaks at 1705 and 1665 cm −1 that resemble the features ascribed to imide carbonyl modes for molecule 7 in Figure 2. The spectrum of 10 further includes an arrow to 1770 cm −1 , which is the location of the strong symmetric anhydride mode observed for PTCDA and molecule 8 in Figure 2.…”

Section: ■ Resultsmentioning

confidence: 78%

“…Similar to Figure , Figure includes representative ATR-IR spectra for tetrakis(butyl)-perylene-3,4,9,10-tetracarboxylate, 9 , for its complete ester conversion and absence of imide or anhydride species as well as for N -( p -trifluoromethylphenyl)-bis(butyl)-perylene-3,4-carboxyimide-9,10-dicarboxylate, 10 , for its mixed ester and one imide functionality. The spectrum of 9 demonstrates features at 1720 and 1706 cm –1 that are characteristic of ester carbonyls . The spectrum of 10 demonstrates peaks at 1705 and 1665 cm –1 that resemble the features ascribed to imide carbonyl modes for molecule 7 in Figure .…”

Section: Resultsmentioning

confidence: 79%

“…Conversions of surface 2a to 3a and of surface 2a to 4a afforded analyses of surface coverage. Solution-based studies of perylene chemistry show that the transformation of PTCDA to tetrakis(butyl)perylene-3,4,9,10-tetracarboxylate 9 is nearly quantitative . For the spectrum of 3a in Figure , the absence of definitive anhydride features confirms a high conversion of terminal anhydrides to ester species, although the small features between 1800 and 1750 cm –1 may be from residual anhydride species.…”

Section: Discussionmentioning

confidence: 94%

“…In contrast to XPS results, the IR chemical features afforded by spectra 2a and 2b are distinct; however, interpreting absorbance values requires knowledge of oscillator strengths that may be affected by interfacial packing and orientation, as well as interactions with the chemically oxidized silicon substrates. Instead, we subsequently utilized the high conversion efficiency for esterification of cyclic anhydride species to incorporate species that are more amenable to coverage analyses. From 2a and 2b , reaction with n -bromobutane respectively yielded 3a and 3b to establish the successful reaction of the surface-exposed anhydride group of 2a and 2b .…”

Section: Resultsmentioning

confidence: 99%

“…Solution-based studies of perylene chemistry show that the transformation of PTCDA to tetrakis(butyl)perylene-3,4,9,10-tetracarboxylate 9 is nearly quantitative. 55 For the spectrum of 3a in Figure 3, the absence of definitive anhydride features confirms a high conversion of terminal anhydrides to ester species, although the small features between 1800 and 1750 cm −1 may be from residual anhydride species. Thus, we believe that the activation of terminal anhydrides and subsequent esterification proceeds at very high, but perhaps not quantitative, yields.…”

Section: Langmuirmentioning

confidence: 85%

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Covalent Attachment and Characterization of Perylene Monolayers on Si(111) and TiO₂ for Electron-Selective Carrier Transport

Carl

Grimm

2019

Langmuir

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We functionalized chemically oxidized Si(111) and TiO2 surfaces with covalently attached rylene molecules and demonstrated further chemical conversion of the attached species. Base-catalyzed activation of perylene tetracarboxylic dianhydride (PTCDA) preceded reaction with phenylaminosilane-terminated surfaces, yielding surface-bound perylene via an imide linkage. Transflection infrared (IR) spectroscopy of the carbonyl vibrational region elucidated the presence of anhydride, imide, and ester species following each reaction stage. The presence of both anhydride and imide IR features following reaction with PTCDA validates successful perylene attachment. Subsequent functionalization of the surface-attached perylenes yielded IR spectra with little or no detectable anhydride features that indicate successful conversion to ester or imide species based on respective reactions with alkyl bromides or aryl amines. X-ray photoelectron spectroscopy quantified fractional coverages of surface-attached perylene species following a post-deposition derivatization with fluorine-containing alkyl bromides and with anilines. Overlayer model interpretation of the photoelectron results determined a perylene surface coverage of ∼15% relative to the surface density of Si(111) atop sites and a ∼10% surface coverage of imide-terminated perylene species. The interpreted coverage data yield an approximate conversion efficiency for the anhydride-to-imide derivatization at surface-attached perylenes of ∼66%. We discuss the present results in terms of possible coverage and packing on oxide-free silicon surfaces and the utilization of covalently attached rylene species as electron-transporting and hole-blocking connecting layers in molecular electronics and tandem-junction photovoltaic designs.

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Section: ■ Resultsmentioning

confidence: 78%

Section: Resultsmentioning

confidence: 79%

Section: Discussionmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Section: Langmuirmentioning

confidence: 85%

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