$re = '/(?<=^# .*⤵(?:\n(?!# ).*)*)\n(^## .*)\n(?!#+ )(.*(?:\n(?!#).*)*)/m';
$str = '# Heading 1 ⤵
## Heading 1.1
Text of Heading 1.1
Text can span over multiple lines
Even more text
## Heading 1.2
Text of Heading 1.2
# Heading 2
## Heading 2.1
Text of Heading 2.1
## Heading 2.2
Text of Heading 2.2
# Heading 3 ⤵
## Heading 3.1
Text of Heading 3.1
## Heading 3.2
Text of Heading 3.2
# Heading 4';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php