Unexpected conversion of a polycyclic thiophene to a macrocyclic anhydride

Kilway, Kathleen V.; Lindgren, K.; Vincent, Joseph W; Watson, James A.; Clevenger, Robert G.; Ingalls, Robert D; Ho, Douglas M.; Pascal, Robert A.

doi:10.1016/j.tet.2003.12.050

Cited by 12 publications

(3 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…C47.8 can alternatively be prepared by refluxing 167.1 with P 4 S 10 in toluene . The compound is of interest because of its diverse reactivity in cycloaddition reactions. − The pyrrole analogue of C47.8 , N -substituted diacenaphtho[1,2- b :1′,2′- d ]pyrrole C47.9 , was synthesized in 2011 by Kawase et al. via a two-step annulation procedure, starting from 1,2-dibromoacenaphthylene (an earlier synthesis of a substituted variant of C47.9 is shown in Scheme , section ).…”

Section: Nonbenzenoid Fusionmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

View full text Add to dashboard Cite

Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

show abstract

Section: Nonbenzenoid Fusionmentioning

confidence: 99%

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

View full text Add to dashboard Cite

show abstract

“…1a), was rst synthesized approximately een years ago but has not drawn much attention. 17,18 Nor have its electronic properties/ Fig. 1 (a and b) Structures of compounds 1 and 2.…”

mentioning

confidence: 99%

“…1a), was rst synthesized approximately een years ago but has not drawn much attention. 17,18 Nor have its electronic properties/ applications been carefully investigated. Herein, we report that spin-coated thin lms of this PAH exhibit unusually high SCLC hole mobility aer thermal annealing.…”

mentioning

confidence: 99%

Unusually high SCLC hole mobility in solution-processed thin films of a polycyclic thiophene-based small-molecule semiconductor

Clevenger

Jin

et al. 2014

J. Mater. Chem. C

View full text Add to dashboard Cite

SCLC hole mobilities up to 8.72 Â 10 À2 cm 2 V À1 s À1 , amongst the highest reported hole mobility values for solution-processed smallmolecule organic semiconductors, are obtained from thermally annealed device-sized thin films of a thiophene-containing polycyclic aromatic hydrocarbon.Charge carrier (hole or electron) mobility is one important parameter affecting the performance of organic electronic/ optoelectronic devices including organic solar cells. 1 The highest hole mobilities (up to $45 cm 2 V À1 s À1 ) for organic semiconductors have been demonstrated on macroscopic, highly ordered, single crystals of conjugated molecules. 2,3 Benetting from the fast advancement of materials chemistry, the hole mobilities of organic-semiconductor thin lms, which are usually prepared by spin-coating or vacuum deposition, have also steadily increased to as high as 12 cm 2 V À1 s À1 . 4,5 Almost all of these high hole mobility values have been obtained by the eld effect transistor (FET) method. Compared to the FET method, which measures the mobility parallel to the electrodes under inuence of a gate bias, the space charge limited current (SCLC) method measures the mobility perpendicular to the electrodes. 6 The SCLC mobility is thus more relevant to solar cells. The FET and SCLC techniques are two of the most widely used methods to investigate charge carrier mobility in organic compounds. The SCLC mobility of organic-semiconductor thin lms is oen lower by a few orders of magnitude than their FET mobility. 6 Despite a few reports of high SCLC mobilities (up to 1.4 cm 2 V À1 s À1 ) measured in mesoscopic/microscopic areas of discotic liquid crystalline conjugated molecules, 3 the SCLC mobilities of macroscopic organic-semiconductor thin lms are generally much lower, ranging from 10 À6 to 10 À4 cm 2 V À1 s À1 . 6-8Among myriads of conjugated molecules, polycyclic aromatic hydrocarbons (PAHs) have drawn the most interest and have been widely investigated for electronic applications. 9-16 Their oen planar or near-planar geometry and extended p-delocalization can induce strong p-p stacking resulting in potentially high charge carrier mobility along the stacked PAH column. 11,15,16 Indeed, the majority of the reported highest SCLC hole mobilities are obtained from PAHs. 2,3 A thiophene-containing fused PAH, namely 2,5,9,12-tetra(tertbutyl)diacenaphtho[1,2-b:1 0 ,2 0 -d]thiophene (DAT) (1) (Fig. 1a), was rst synthesized approximately een years ago but has not drawn much attention. 17,18 Nor have its electronic properties/ Fig. 1 (a and b) Structures of compounds 1 and 2. Energy-minimized geometries of 1 (c and e) and 2 (d and f) from different views obtained using DFT calculations at the B3LYP/6-31G(d) level. † Electronic supplementary information (ESI) available: Experimental details; synthesis and characterization of 1 and 2; visualized LUMO+1, LUMO, HOMO and HOMOÀ1 orbitals of the energy-minimized conformers; UV-vis absorption and orescence emission spectra; cyclic voltammograms; DSC thermograms. See

show abstract

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Guziec

2022

Organic Reactions

View full text Add to dashboard Cite

Extrusion reactions may be defined as chemical reactions in which an atom or small molecular fragment Y connected to two other atoms W and Z is lost from a molecule, leading to a product in which W becomes directly bonded to Z. Cheletropic reactions that afford aromatic or conjugated π systems by loss of a stable atomic or molecular fragment have also been classified as extrusion reactions. Typically, the fragments liberated in these reactions are small, stable inorganic molecules or atoms such as carbon monoxide, carbon dioxide, sulfur, sulfur monoxide, sulfur dioxide, selenium, tellurium, oxygen and nitrogen. This chapter primarily deals with the synthesis of arenes, heterocycles, 1,3‐dienes and polyenes using such extrusion processes. The utility of these reactions in the synthesis of sterically hindered molecules, dendrimers, pheromones, and other natural products are highlighted. The use of extrusion reactions for the “Click and Release” approach in drug development is also introduced.

show abstract

Unexpected conversion of a polycyclic thiophene to a macrocyclic anhydride

Cited by 12 publications

References 6 publications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Unusually high SCLC hole mobility in solution-processed thin films of a polycyclic thiophene-based small-molecule semiconductor

Extrusion Reactions Affording Aromatic Systems, Dienes and Polyenes

Contact Info

Product

Resources

About