Serendipitous Formation of Semiconducting Semi-Nindigo Indigoid by the Degradation of Diindolopyrrole

Abstract

We report the serendipitous discovery and synthesis of an indigoid “semi-Nindigo” (2) via oxidation of a diindolopyrrole (1). The reaction of 2 with BF3Et2O affords the borylated derivative (3). The electronic spectra of 2 and 3 possess intense long wave absorptions near 600 and 650 nm. Compound 3 is weakly emissive in the near-infrared. Thin-film OFETs fabricated with 1 and 2 both exhibited hole mobility of 10–5 and 10–3 cm2/(V s), respectively.

Band gap engineering of donor–acceptor co-crystals by complementary two-point hydrogen bonding

“…By itself, DIP 1 is a p-type OSC which shows a modest hole mobility of 10 À5 cm 2 V À1 s À1 in vacuum deposited films. 54 To our knowledge, there has been no report of OFETs based on compound e. We were able to prepare thin-film OFETs by co-sublimation of the H-bonded complex 1 2 e powder, although efforts to co-sublime complexes of 1 with more volatile acceptors (c and d) led to deposition of the individual acceptor component. The film of 1 2 e exhibited red-shifted CQO and N-H vibrations compared to the individual donor/acceptor components which is indicative of a reduction in bond order due to H-bonding, and displayed a low energy CT absorption resembling that of the solid 1 2 e (Fig.…”

Electric-Field-Induced Effects on the Dipole Moment and Vibrational Modes of the Centrosymmetric Indigo Molecule

“…Here, we present a computational DFT investigation of the effects induced by the application of OEEFs on the indigo molecule (Figure ). In the last few years, a growing interest in indigoid species has been recorded, with a particular focus on their applications in several branches ranging from photodiodes to organic field-effect transistors (OFETs). − Indigo owes its fame to its own peculiar natural blue color and has been extensively used in art and textiles since very ancient times. IR absorption and Raman scattering are effective methods for the identification and characterization of pigments and dyes in the field of cultural heritage.…”

High-performance five-ring-fused organic semiconductors for field-effect transistors

“…The main reasons for the low performance are the edge-to-face packing and poor p-orbital overlap resulting from the self-complementary H-bonding interactions. 352 The performance statistics of five-ring-fused organic semiconductors in Fig. 25 are shown in Table S17 of the ESI.…”

“…The main reasons for the low performance are the edge-to-face packing and poor π-orbital overlap resulting from the self-complementary H-bonding interactions. 352…”