Modulating the ground state, stability and charge transport in OFETs of biradicaloid hexahydro-diindenopyrene derivatives and a proposed method to estimate the biradical character

Abstract

Biradicaloid compounds with an open-shell ground state have been the subject of intense research in the past decade. Although diindenoacenes are one of the most developed families, only few examples...

Characterization of Benzo[a]naphtho[2,3‐f]pentalene: Interrelation between Open‐shell and Antiaromatic Characters Governed by Mode of the Quinoidal Subunit and Molecular Symmetry

“…Singlet open‐shell molecules [1–6] have been intensively investigated for a decade using both experimental and theoretical approaches. Not only are their unique electronic structures scientifically intriguing, they have potential in applications as organic optoelectronic materials [7] such as field‐effect transistors, [8–14] nonlinear optics, [15–17] and singlet fissions [18–20] . The singlet open‐shell character, which often inhabits o ‐ or p ‐quinoidal subunits in polycyclic hydrocarbons, [6,21–24] is frequently associated with the aromatic or antiaromatic nature due to an inherently small HOMO‐LUMO gap [25–27] .…”

Synthesis, crystal structure and charge transport characteristics of stable peri-tetracene analogues

“…However, the time-dependent (TD)-DFT calculations showed a larger vertical excitation energy of TBP5 than TBP4 for the triplet in the singlet ground state geometry, suggesting that the different activation energies for the triplet caused the different degrees of broadening. Because some recent papers have reported a high biradical character with a large Δ E S–T , 23,24 this should be investigated in more detail in future works.…”

“…Some recent reports used several types of singlet biradical compounds for the active layer of OFETs, which revealed their bipolar transport owing to small energy gaps. [24][25][26] The TBP-based devices also demonstrated a capability of bipolar transport for peri-acene derivatives. Fig.…”

Essential Role of Triplet Diradical Character for Large Magnetoresistance in Quinoidal Organic Semiconductor with High Electron Mobility

“…Unlike other diradical semiconductor materials, which show either ambipolar or p‐type transport properties, [ 34–38 ] DTBDTCN exhibited n‐type transport property. Moreover, all the devices showed similar performance in air and under an N 2 atmosphere, indicating the high ambient stability of DTBDTCN devices owing to the deep LUMO energy level.…”