B2,N4-Doped Heptacenes: Ambipolar Charge-Transfer Compounds with Deep LUMO Levels

M Metzler, A Virovets, HW Lerner… - Journal of the American …, 2023 - ACS Publications
The B2, N4-doped heptacene H4 in which two N, N′-dihydrophenazine units are linked by
two BMes bridges (Mes= mesityl) was synthesized via fourfold Buchwald− Hartwig coupling …

BNB-doped phenalenyls: modular synthesis, optoelectronic properties, and one-electron reduction

AS Scholz, JG Massoth, M Bursch… - Journal of the …, 2020 - ACS Publications
A highly modular synthesis of BNB-and BOB-doped phenalenyls is presented. Treatment of
the 1, 8-naphthalenediyl-bridged boronic acid anhydride 1 with LiAlH4/Me3SiCl afforded the …

The most stable and fully characterized functionalized heptacene

D Chun, Y Cheng, F Wudl - Angewandte Chemie, 2008 - Wiley Online Library
Theoretical calculations predict a narrowing of band gap energies in the acene family with
each successive benzene ring addition up to hexacene, beyond which the HOMO–LUMO …

Triphenylene Analogues with B2N2C2 Cores:  Synthesis, Structure, Redox Behavior, and Photophysical Properties

CA Jaska, DJH Emslie, MJD Bosdet… - Journal of the …, 2006 - ACS Publications
A series of alkyl (1− 3), aryl (6), and benzo-annulated (4, 5) heteroaromatic triphenylene
analogues with B2N2C2 cores have been synthesized via chelation of pyridazine …

“Butterfly Wings” stabilize heptacene

M Müller, EC Rüdiger, S Koser… - … A European Journal, 2018 - Wiley Online Library
The synthesis of bisalkynylated derivatives of tetrabenzo [a, c, p, r] heptacene and
tetrabenzo [a, c, l, n] pentacene via two‐/fourfold Stille reactions involving a 9 …

Persistent ambipolar heptacenes and their redox species

N Zeitter, N Hippchen, S Maier… - Angewandte Chemie …, 2022 - Wiley Online Library
Sixfold TIPS‐ethynylation combined with fourfold bromination of the armchair edges
furnishes a long‐lived, soluble heptacene; π‐extension via Stille coupling accesses a …

Heteroheptacenes with fused thiophene and pyrrole rings

P Gao, D Cho, X Yang, V Enkelmann… - … A European Journal, 2010 - Wiley Online Library
The preparation of conjugated heteroheptacenes using an electrophilic coupling reaction
induced by a super acid is reported. The new molecules containing thiophene and/or pyrrole …

Mixed‐Valent Molecular Triple Deckers

HC Schmidt, X Guo, PU Richard… - Angewandte Chemie …, 2018 - Wiley Online Library
Two phenothiazine (PTZ) moieties were connected via naphthalene spacers to a central
arene to result in stacked PTZ‐arene‐PTZ structure elements. Benzene and …

Highly stable organic bisradicals protected by mechanical bonds

K Cai, H Mao, WG Liu, Y Qiu, Y Shi… - Journal of the …, 2020 - ACS Publications
Two new highly charged [2] catenanes—namely, m He [2] C· 6PF6 and m Ho [2] C· 6PF6—
were synthesized by exploiting radical host–guest templation between derivatives …

Synthesis and properties of a twisted and stable tetracyano-substituted tetrabenzoheptacene

M Martínez-Abadía, G Antonicelli, E Zuccatti… - Organic …, 2017 - ACS Publications
An approach for the synthesis of pyrene-fused acenes that allows the introduction of electron-
withdrawing cyano groups in key positions that simultaneously (i) induce twists in the …