Design and synthesis of benzothiadiazole-based molecular systems: self-assembly, optical and electronic properties

Abstract

A set of small benzothiadiazole (BTD)-based derivatives with a D-A-D architecture was synthesized and characterized as building blocks of organic semiconducting materials by applying an experimental-theoretical approach. The four derivatives...

Benzothiadiazole-based fluorophores as efficient non-doped emitters for solution-processed organic light-emitting diodes

“…The reduction process of both molecules occurred at nearly the same half-wave potential ( E 1/2 ) of ∼−1.40 eV, assigned to the reduction of the Bz unit. 9,66 The first oxidation wave appeared at E 1/2 of 1.25 V for CPBFPhC and 0.91 V for CPBFTPA could be related to the oxidation of 3,6-di- tert -butylcarbazole 34,35,67 and (4-(diphenylamino)phenyl)fluorene moieties, 39,68,69 respectively, forming radical cations. The lower first oxidation potential of CPBFTPA as compared to that of CPBFPhC is well consistent with the shallower calculated HOMO level (−4.97 eV) of CPBFTPA than that of CPBFPhC (−5.12 eV) (Fig.…”

An efficient solution-processable non-doped hybridized local and charge-transfer (HLCT) emitter for a simplified organic light-emitting diode

“…The reduction wave occurring at a half-wave potential (E 1/2 ) of À1.39 eV could be assigned to the Bz unit reduction. 67,68 The first oxidation wave occurring at an E 1/2 of 1.15 V could be related to the oxidation of 3,6-di-tert-butylcarbazole moiety forming radical cations, 41,42,69 while the second oxidation wave at an E 1/2 of 1.38 V could be attributed to the oxidation of the p-conjugated 4-(7-(carbazol-N-yl)fluoren-2-yl)benzothiadiazole fragment. Additionally, the repeated CV scans exhibited unchanged CV traces implying that PBzFC is an electrochemically stable molecule (Fig.…”

Dual Hybridized Local and Charge Transfer Characteristic Fluorophore as an Efficient Nondoped Emitter for Electroluminescent Device

“…The CV results revealed ambipolar redox types comprising quasireversible reduction and oxidation processes (Figure 5c and Table 1). The first reduction wave at halfwave potential ( E 1/2 ) around −1.3 eV could be assigned to the Bz unit reduction, [5a,27] while the first oxidation wave at E 1/2 of 1.09 V could be ascribed to the oxidation of 3,6‐di‐ tert ‐butylcarbazole moiety. [ 28 ] Based on the onset oxidation potential, the HOMOs of BCBF and CBF were calculated to be −5.47 eV, and then their LUMOs were deduced from the HOMOs and optical bandgaps ( E g opt ) to be −3.03 and −2.98 eV, respectively (Table 1).…”