BODIPY dyads and triads: synthesis, optical, electrochemical and transistor properties

Abstract

A series of D–A dyads and D–A–D triads molecular systems based on triphenylamine and 9-ethyl-carbarzole as donor (D) and BODIPY as acceptor (A) has been designed and synthesized. The optoelectronic properties including optical, electrochemical, and charge carrier mobility of these molecules have been investigated. We found that the D–A–D triads exhibited broader absorption, raising the HOMO energy levels and increase hole carrier mobilities. Analysis surface morphology revealed that BODIPY containing carbazole demonstrated smooth film and no macro phase aggregation was observed upon thermal annealing. Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0430-5) contains supplementary material, which is available to authorized users.

Improved Performance of Ternary Solar Cells by Using BODIPY Triads

“…Our target BODIPY compounds, TPA-BODIPY-TPA (BODIPY-1) and CBZ-BODIPY-CBZ (BODIPY-2) (Figure 1), were synthesized following our previous report [49]. The chemical structures were confirmed using 1 H-NMR and 13 C-NMR, respectively (see Supplementary Materials, Figures S1-S6).…”

“…Figure 7 presents the energy diagram of donor and acceptors. The HOMO and LUMO energy levels of BODIPY-1 and BODIPY-2 were estimated from our previous study [49]. The HOMO and LUMO offset (∆E) values between P3HT and BODIPY are about ∼0.1-0.2 eV, which are energetically feasible in term of driving the cascade charge transfer from P3HT to BODIPY and from BODIPY to PCBM [19,20].…”

“…According to our previous report, we synthesized BODIPY triads containing triphenylamine (TPA) and carbazole (CBZ) groups. These BODIPY triads showed an absorption maxima at 540 nm with moderate hole carrier mobilities [49]. Therefore, we are interested to incorporate BODIPYs triads as the second donor in Therefore, we are interested in incorporating BODIPYs triads as the second donor in P3HT:PCBM solar cell.…”

Carbazole Substituted BODIPYs

“…Wanwong et al reported the application of beta -carbazole substituted BODIPY dyad and triad (Scheme 5; 15 and 16) as field effect transistors (FET). Though these derivatives provided moderate performance, modification of this structure may help to develop better dye with better performance (Wanwong et al, 2018).…”

meso-Carbazole decorated BODIPYs – an electron donor–acceptor system with excellent fluorosolvato/vapochromic behavior, aggregation-induced emission, and antileishmanial activity

“…[22][23][24]33 It is reported that the absorption and emission behavior of BODIPYs can be modified by the presence of an electron-rich carbazole moiety. 25,26 The linkage and the position at which carbazole is attached to the BODIPY scaffold play a major role. The structural diversity of the carbazole-BODIPY conjugates includes the BODIPY derivatives with carbazole rings at the alpha, beta, and meso-positions of the BODIPY skeleton.…”