The crucible of time
by John Brunner · first published 1983
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https://www.researchgate.net/publication/253117230_Science_F... - which may or may not have specific items in it that you're after, but they are on the harder side of science fiction within the topic. I'd also suggest Crucible of Time by John Brunner, while it doesn't have black holes it does have an astronomical time pressure to it. Flux is part of Stephen Baxter's Xeelee Sequence and again has an astronomical pressure. I'm gonna…
on “A Sun-like star orbiting a black hole” ↗…moon, creating cities, tried to harvest asteroids but accidentally wiped themselves out after a major mistake, eliminating the evidence for their civilization in the process. This was after reading The Crucible of Time by Brunner (one of my favourite books)
on “The Next Ten Billion Years” ↗Johm Brunner's The Crucible of Time. There are only aliens in that book, even if the aliens behave quite humanly. https://en.wikipedia.org/wiki/The_Crucible_of_Time
on “Science Fiction Books About Aliens” ↗