Synthesis, Molecular Packing, and Thin Film Transistors of Dibenzo[a,m]rubicenes

Abstract

We herein report an efficient synthesis of dibenzo[a,m]rubicene, a new member of nonplanar cyclopenta-fused polycyclic aromatic hydrocarbon, and its derivatives. It is found that the conformation and molecular packing of dibenzo[a,m]rubicenes in the solid state can be tuned by the substituting groups, and the silylethynylated derivatives of dibenzo[a,m]rubicenes function as p-type organic semiconductors in solution-processed thin film transistors with field effect mobility of up to 1.0 cm(2) V(-1) s(-1).

Fused Dibenzo[a,m]rubicene: A New Bowl-Shaped Subunit of C70 Containing Two Pentagons

“…Thus far, most studies on fullerene chemistry have been focused on the synthesis of bowl-shaped molecules as subunits of fullerene C 60 , the synthesis of fragments of C 70 remains elusive mostly due to the lack of proper synthetic protocols as well as their accessibility in reasonable amounts. [ [26,27] derivative as the key reaction (Scheme 1). Compound 1, with 34 carbon atoms, is a fragment for investigating C 70 , because it contains all the types of carbon atoms present in C 70 (Scheme 1).…”

A Stable Saddle‐Shaped Polycyclic Hydrocarbon with an Open‐Shell Singlet Ground State

“…The crystal structure unambiguously shows an ovel saddle-shaped pconjugated carbon skeleton due to the steric hindrance of the central cove-edged bischrysene unit. [10] Therefore,t he development of diindeno-fused PHs bridged with novel p-expanded skeletons is highly attractive.Herein, we report anovel saddle-shaped cyclopenta-fused PH, namely,t he diindeno-fused bischrysene DFB 1 (Figure 1b), in which the curved bischrysene [11] core has been extended with two indene units.T he design strategy considered the following two aspects:a )The incorporated bischrysene scaffold possesses ac urved conformation due to the steric hindrance of hydrogen atoms in the cove region, and adopts a p-bond-localized resonance structure in the solid state, [11,13] which is different from that in fully benzenoid polycyclic aromatic hydrocarbons (PAHs); [12] b) extending the p-conjugated bridge with the fused bischrysene leads to al ow energy gap in the system. [1] Several types of open-shell PHs have been constructed by using bisphenalenyl, [2] zethrene, [3] and anthene [4] building blocks.F urthermore,m uch effort has been devoted to the synthesis of stable diindeno-based PHs by fusing two indene units into a p-conjugated bridge, [5] owing to their narrow energy gaps,the singlet fission phenomenon, and their potential proaromatic features.…”

Facile Synthetic Approach to a Large Variety of Soluble Diarenoperylenes

“…[5b, 6] Other examples are phenylenetetracene, a2 D-fused p-system based on tetracene, giving hole mobilities of 0.01 cm 2 V À1 s À1 , [7] or dibenzorubicene with hole mobilities of 1.0 cm 2 V À1 s À1 . [8] There are also af ew acene systems stabilized with six-membered fused rings described as materials for organic TFTs. For instance, Perepichka et al described two isomeric dibenzoperylenes, where one is an insulator and the other one shows electron mobilities of 0.04 cm 2 V À1 s À1 and ah ole mobility of 0.002 cm 2 V À1 s À1 .…”