Quinoidal Naphtho[1,2‑<i>b</i>:5,6‑<i>b</i>′]dithiophenes for Solution-Processed n‑Channel Organic Field-Effect Transistors

A series of new quinoidal naphtho­di­thio­phenes, 2,7-bis­(α,α-di­cyano­methylene)-2,7-di­hydro­naphtho­[1,2-<i>b</i>:5,6-<i>b</i>′]­di­thio­phenes, in which all the four fused aromatic rings are incorporated into the quinoidal system, were synthesized and evaluated as an n-channel organic semiconductor. Solution-processed field-effect transistors exhibited typical n-channel transistor characteristics with the mobility as high as 0.1 cm² V^–1 s^–1, which is higher by more than 1 order of magnitude than those reported for isomeric quinoidal naphtho­di­thio­phenes having a naphtho­quinoidal structure

Dithiophene-Fused Tetra­cyano­naphtho­quino­dimethanes (DT-TNAPs): Synthesis and Characterization of π‑Extended Quinoidal Compounds for n‑Channel Organic Semiconductor

Dithiophene-fused tetra­cyano­naphtho­quino­dimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (∼4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, α-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10^–3 cm² V^–1 s^–1, indicating that DTTNAPs are a potential molecular framework for n-channel organic semiconductors

Dithiophene-Fused Tetra­cyano­naphtho­quino­dimethanes (DT-TNAPs): Synthesis and Characterization of π‑Extended Quinoidal Compounds for n‑Channel Organic Semiconductor

Dithiophene-fused tetra­cyano­naphtho­quino­dimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (∼4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, α-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10^–3 cm² V^–1 s^–1, indicating that DTTNAPs are a potential molecular framework for n-channel organic semiconductors

Dithiophene-Fused Tetra­cyano­naphtho­quino­dimethanes (DT-TNAPs): Synthesis and Characterization of π‑Extended Quinoidal Compounds for n‑Channel Organic Semiconductor

Dithiophene-fused tetra­cyano­naphtho­quino­dimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (∼4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, α-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10^–3 cm² V^–1 s^–1, indicating that DTTNAPs are a potential molecular framework for n-channel organic semiconductors

Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation

Selective functionalization protocols of naphtho[1,2-<i>b</i>;5,6-<i>b</i>′]dithiophene (NDT3) by combining protection of the thiophene α-positions and direct borylation on the naphthalene core are described, which allows synthesizing a number of new NDT3-based building blocks with various substituents and isomeric NDT3-based polymers with different main chain structures. The same protocol is applicable to other isomeric naphthodithiophenes (NDTs), which affords a set of key building blocks for the development of elaborated functional π-materials

Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation

Selective functionalization protocols of naphtho[1,2-<i>b</i>;5,6-<i>b</i>′]dithiophene (NDT3) by combining protection of the thiophene α-positions and direct borylation on the naphthalene core are described, which allows synthesizing a number of new NDT3-based building blocks with various substituents and isomeric NDT3-based polymers with different main chain structures. The same protocol is applicable to other isomeric naphthodithiophenes (NDTs), which affords a set of key building blocks for the development of elaborated functional π-materials