Abstract
Two s-shaped polyaromatic dibenzo[c,l]chrysene derivatives have been synthesized by a two-step process, via. The Wittig reaction, followed by iodine, promoted photocyclization. These molecules have been characterized by 1H NMR, FAB-MS, and elemental analysis. Further, the molecular structures of 4a and 4b have been confirmed by single crystal X-ray diffraction analysis. The protons located in the cove-regions of molecules 4a and 4b showed downfield shifts of the protons. Molecule 4a crystallized under the monoclinic system with space group C2/c, and the molecule 4b crystallized under the monoclinic system with space group P21/n. Molecules 4a and 4b showed strong absorption maxima wavelengths at 310 nm and 324 nm, respectively. The molar extinctinction coefficients (ε) of the compounds 4a and 4b indicated that molecule 4b has a better ability to absorb UV light than molecule 4a. The emission spectra of the molecules 4a and 4b displayed peaks in the region 429–456 nm. The shape of the UV-Visible and Fluorescence spectra of the molecules 4a and 4b look almost identical. However, molecule 4b exhibited better fluorescence intensity than molecule 4a. This may be due to the difference in the substituents of molecules 4a and 4b.
Highlights
Polyaromatic hydrocarbons or π-conjugated materials are an important class of organic compounds because their important property of conductivity led to tremendous advancements in the field of organic electronics [1]
Over the past decade significant research has been done and the search for the new π-conjugated systems has been ongoing because of the important, rapidly growing number of applications in electronic devices such as semiconducting materials [2,3,4,5], organic solar cells [6], sensors [7], organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), and flexible displays. π-conjugated materials have been extensively studied for their optoelectronic properties due to the offering of low-cost, large-area, and flexible electronic devices [8,9,10]
Spectra-naphthalene dichloride 1 was condensed with 2,3,4,5-tetrafluoro or Molecules 4a and 4b have been synthesized in two steps
Summary
Polyaromatic hydrocarbons or π-conjugated materials are an important class of organic compounds because their important property of conductivity led to tremendous advancements in the field of organic electronics [1]. S-shaped dibenzo[c,l]chrysene derivatives are regarded as a hexacyclic polyaromatic hydrocarbon compound containing two cove-regions, and they have potential applications in biological systems and organic semiconductor materials [11,12]. The synthesis of s-shaped benzo[c,l]chrysene derivatives is of great interest, and is challenging because of the steric hindrance in the cove-regions. Crystals 2017, 7, 251 benzo[c,l]chrysene derivatives with substituents like -F, -CF3 in the cove-region is even more challenging because of the increased steric hindrance. An ideal organic electronic material should have a low HOMO (highest occupied molecular orbital)-LUMO unoccupied molecular orbital) energy shaped benzo[c,l]chrysene derivatives with
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