Thiophene-fused bowl-shaped polycyclic aromatics with a dibenzo[a,g]corannulene core for organic field-effect transistors

Abstract

For the first time, electron-rich thiophene units were fused into the skeleton of corannulene to extend π-surfaces and tune arrangement in single crystals. Two isomeric butterfly-like thiophene-fused dibenzo[a,g]corannulenes (3 and 5) were synthesized. Isomer 3 showed p-type transport properties, with a hole mobility of 0.06 cm(2) V(-1) s(-1).

Electronic transport properties of selected carbon π-bowls with different size, curvature and solid state packing

“…Corannulene, the smallest non-planar fragment of C 60 fullerene [5,6], was shown to exhibit high degree of lithium intercalation upon step-wise reduction [7][8][9][10] and corannulene-based anode materials have demonstrated a high reversible lithium capacity, almost twice as high as that of fully lithiated graphite [11,12]. The family of p-bowls also provides a natural platform for designing new organic materials with applications in light emitting-diodes [13][14][15][16], field-effect transistors [17][18][19], or photovoltaic cells [20]. While organic semiconductors may still not compete with their inorganic counterparts in terms of charge-carrier mobility or power efficiency performance, they do have the advantage of being low-cost, flexible, easily processable in solution, and compatible with many substrates [21,22].…”

“…In particular, p-p bowl interactions between molecules of the indenocorannulene family with strong dipole moments promote a one-dimensional (1D) columnar stacking which, in turn, should favor an efficient channel for charge transport. Experimental studies on sumanene [44] and corannulene derivatives [17][18][19][20]45] important and timely to carry out a careful theoretical investigation in order to understand their potential as active materials in organic electronic devices.…”

Light‐Insensitive Organic Field‐Effect Transistors with n‐Type Conjugated Polymers Containing Dinitrothiophene Units

“…[16][17][18] Considering that the thickness of channel layers in OFETs is usually in the range of ≈50 nm or less, a reasonable transparency can be made if electrodes are transparent (metal oxides) or semitransparent (metals). [23][24][25][26][27] Therefore, light-insensitive organic semiconducting materials are required to achieve real transparent OFETs without large disturbance by surrounding light. [23][24][25][26][27] Therefore, light-insensitive organic semiconducting materials are required to achieve real transparent OFETs without large disturbance by surrounding light.…”

Synthesis of Rationally Halogenated Buckybowls by Chemoselective Aromatic C−F Bond Activation

“…[1][2][3] Because of the tremendous strain inherent to the geodesic structure,t he fabrication of buckybowls frequently requires harsh reaction conditions that do not tolerate functional groups.Asaresult, the controllable functionalization of the buckybowl system still remains ac hallenge,t hus hampering further development in this field. Appropriate functionalized buckybowls are important starting materials for further derivatization [4][5][6][7][8][9][10][11][12][13][14][15][16] and key building blocks for the rational synthesis of fullerenes, nanotubes,a nd other related carbon-based nanostructures by abottom-up strategy. [17][18][19][20][21][22][23][24][25][26] In this respect, halogenated, and in particular brominated, bowls appear to be the most important derivatives.…”

“…[17][18][19][20][21][22][23][24][25][26] In this respect, halogenated, and in particular brominated, bowls appear to be the most important derivatives. [4][5][6][7][8][9][10][11][12][13][14][15][16] Themost often studied approaches to buckybowls are based on the intramolecular aryl-aryl coupling of appropriate precursor molecules by means of flash vacuum pyrolysis (FVP), [2,27] surface-assisted cyclodehydrogenation, [28][29][30][31] and palladium-catalyzed direct arylation methods. [32][33][34][35][36] Unfortunately,n one of these methods can be applied to the synthesis of halogenated BS-PAHs.A lthough the postsynthetic halogenation of corannulene,t he smallest buckybowl, has proven to be effective, [37,38] this approach is not effective in the case of large and less symmetrical molecules.T hus,t he development of new methods that enable the facile synthesis of halogenated BS-PAHs in af ully controllable way is am atter of great interest and importance.…”