Contorted Tetrabenzocoronene Derivatives for Single Crystal Field Effect Transistors: Correlation between Packing and Mobility

Abstract

A series of contorted tetrabenzo[a,d,j,m]coronenes (TBCs) substituted with four fluoro-, chloro-, or methyl groups at 2,7,12,17-positions were synthesized and characterized. Except for the one with methyl substituents, which exhibits a shifted π–π stacking, the rest all show cofacial π–π stacking with small parallel displacements. One-dimensional growth along the stacking direction was observed in the single crystals for all derivatives. A systematic comparison of the crystal packing and the calculated electronic coupling/mobility with the measured field-effect mobility for single-crystal field-effect transistors shows a good correlation.

New Charge‐Transfer Complexes with 1,2,5‐Thiadiazoles as Both Electron Acceptors and Donors Featuring an Unprecedented Addition Reaction

“…Fast progress in materials science on organic electronics and optoelectronics is predominantly relatedt oo rganic semicon-ductors.G enerally, those are low-or high-molecular-weight pdelocalized compounds. [1] Research into organic semiconductors began with smallm olecules, particularly with their chargetransfer (CT) complexes [2] formed by interactions between p-electron donor (D) and p-electron acceptor (A) molecules. [3] Both low-and high-molecular-weight CT complexes are of interest to the field, including new applicationsc overing ambipolar transport, metallicity,p hotoconductivity,f erroelectricity, or magnetoresistance.…”

Rational design of bio-inspired high-performance ambipolar organic semiconductor materials based on indigo and its derivatives

“…For indigo substituent derivatives 1-12, no great reorganization energy reducing has been observed. Especially, the cyanide and halogenation substitutions with weak electron-withdrawing groups (-Cl, -Br) have been widely regarded as efficient reorganization energy reducing strategies based on structural modifications [54][55][56][57], but for molecules 1-12, these strategies become invalid. Contrary to expectations, the k h s of 6,6 0 -positions substituent molecules surprisingly are much larger than indigo and for halogen substitutions, even larger k e s are simultaneously generated.…”

Deciphering the Multifarious Charge‐Transport Behaviour of Crystalline Propeller‐Shaped Triphenylamine Analogues

“…The process of crystallisation is one method for regulating the charge‐carrier characteristics of organic materials because molecular ordering and the packing arrangement of the molecules in crystals play a huge role in modulating the charge‐transport abilities . The crystalline architectures that encompass higher degrees of intermolecular orbital overlap enhance the mobility of charges throughout the organic charge transporters . The propeller‐shaped triphenylamine (TPA) core has gained immense interest for HTMs in OLEDs, owing to good thermal stability, a high glass transition temperature, and efficient hole‐transporting ability coupled with low ionisation potential .…”

“…[9] The crystalline architectures that encompass higherd egreeso fi n-termolecular orbital overlap enhancet he mobility of charges throughout the organic charge transporters. [10][11][12][13][14][15] The propeller-shaped triphenylamine (TPA) core has gained immense interestf or HTMs in OLEDs, owing to good thermal stability,a high glass transition temperature, and efficient hole-transporting ability coupled with low ionisation potential. [8,[16][17][18][19][20] Functionalisationo ft he TPAm olecule would result in diverse crystallinep acking arrangements, [21] which, in turn, couldf ine-tune the optoelectronic properties of the core TPAm oiety by enhancing the p-p interorbital interaction between phenyl rings.…”