Amphiphilic (Phthalocyaninato) (Porphyrinato) Europium Triple-Decker Nanoribbons with Air-Stable Ambipolar OFET Performance

Abstract

An amphiphilic mixed (phthalocyaninato) (porphyrinato) europium­(III) triple-decker complex [Pc­(OPh)₈]­Eu­[Pc­(OPh)₈]­Eu­[TP­(CCCOOH)­PP] (<b>1</b>) with potential ambipolar semiconducting HOMO and LUMO energy levels has been designed, synthesized, and characterized. The OFET devices fabricated by quasi-Langmuir-Shäfer (QLS) technique at the air/water interface with nanoparticle morphology display hole mobility of 7.0 × 10^–7 cm² V^–1 s^–1 and electron mobility of 7.5 × 10^–7 cm² V^–1 s^–1, which reflects its ambipolar semiconducting nature. However, the performance of the devices fabricated via a “phase-transfer” method from <i>n</i>-hexane with one-dimensional nanoribbon morphology was significantly improved by 3–6 orders of magnitude in terms of hole and electron mobilities, 0.11 and 4 × 10^–4 cm² V^–1 s^–1, due to the enhanced π–π interaction in the direction perpendicular to the tetrapyrrole rings associated with the formation of a dimeric supramolecular structure building block depending on the intermolecular hydrogen bonding between the neighboring triple-decker molecules in the one-dimensional nanoribbons