Synthesis and fluorescence emission properties of D-π-D monomers based on dithieno[3,2-b:2′,3′-d]thiophene

Abstract

We herein present four highly fluorescent and stable D-π-D monomers (2), which were designed and synthesized using different types of aryl substituent as the donor via a Suzuki-Miyaura coupling reaction. We have studied these four symmetrical chromophores by UV-vis absorption and fluorescence emission spectroscopy both in solution and the solid state. This research shows that the introduction of the aryl groups can effectively extend the conjugation length of thiophene chromophore resulting in a shift of the wavelength of the absorption and fluorescence emission and an improvement of the fluorescence quantum yields. The notable optical features of their solid-state powders also exhibited a distinct red-shift in comparison with the emissions of their dilute solutions. These results combined with the theoretical calculations (B3LYP/6-31G*) indicate that these systems are promising candidates in the fabrication of organic electroluminescence devices.

Dithieno[3,2-b:2′,3′-d]thiophene (DTT): an emerging heterocyclic building block for future organic electronic materials & functional supramolecular chemistry

“…The authors have studied these versatile chromophores both in solid as well as solution state through UV-vis absorption and fluorescence spectroscopic means ( Scheme 12 ). 93 Fascinatingly, they noticed that incorporation of the aryl groups extends the conjugation and reduce the HOMO–LUMO gap of the thiophene chromophore, thereby red-shift in the wavelength of both absorption as well as emission. The remarkable optical signatures of their solid state powders also unveiled a discrete red-shift than the emissions of their dilute solutions.…”

Absorption and fluorescence spectra of new pyrrolo[3,4‐b]quinolizines in condensed phases: A joint experimental and computational study

“…Fluorescence is currently used for their wide applicability in life science, material science, and engineering [1][2][3]. Organic fluorescent molecules, especially heterocyclic compounds, are of interest because of their simplicity, low cost-effectivity, and ability to tune the emission wavelength by synthetic chemical modifications [4,5]. Therefore, the development of practically fluorescent heterocyclic compounds is ongoing.…”