Machine Learning, Divergent Syntheses, and X-ray Analyses of Dithienobenzothiazole-based Semiconductors Controlled by S•••N and S•••S Interactions

18 March 2024, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


Inspired by the previous machine-learning study that the number of hydrogen-bonding acceptor (NHBA) is important index for the hole mobility of organic semiconductors, we synthesized seven dithienobenzothiazole (DBT) derivatives 1a–g (NHBA = 5) by one-step functionalization from a common precursor. X-ray single-crystal structural analyses confirmed that the molecular arrangements of 1b (the diethyl and ethylthienyl derivative) and 1c (the di(n-propyl) and n-propylthienyl derivative) in the crystal are classified into brickwork structures with multidirectional intermolecular charge-transfer integrals, as a result of incorporation of multiple hydrogen-bond acceptors. The solution-processed top-gate bottom-contact devices of 1b and 1c had hole mobilities of 0.16 and 0.029 cm2 V–1s–1, respectively.


Organic synthesis
Crystal structure
Organic semiconductor
Organic field-effect transistors
DFT calculation

Supplementary materials

Supplementary data
Supplementary data for the manuscript


Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.